Brown Lab
Indiana University

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71

Photochemical Reduction of Quinolines with γ-Terpinene

Souvik Adak, Sarah E. Braley, and M. Kevin Brown

Org. Lett. 2024, 26, 1, 401–405.Links to Publication


70

Ni-Catalyzed 1,1- and 1,3-Aminoboration of Unactivated Alkenes

Mao-Yun Lyu, Gabriel N. Morais, Shuming Chen*,‡ and M. Kevin Brown*,†

J. Am. Chem. Soc. 2023 145, 50, 27254–27261.

 

-Highlighted in ChemistryViews 

-Highlighted in  Synfacts 2024; 20(03): 0278 


69

Synthesis of 2-Azanorbornanes via Strain-Release Formal Cycloadditions Initiated by Energy Transfer

Yu-Che Chang, Christophe Salome, Thomas Fessard,*and M. KevinBrown*

Angew. Chem. Int. Ed. 2023, 62, e202314700 

 

-Featured in the February edition of “Some Items of Interest to Process R&D Chemists and Engineers  Org. Process Res. Dev. 2024


68

Photosensitized [2 + 2]-Cycloadditions of Dioxaborole: Reactivity Enabled by Boron Ring Constraint Strategy

Yanyao Liu and M. Kevin Brown

J. Am. Chem. Soc., 2023, 145, 2506125067.

-Highlighted in Synfacts, 2024; 20(02): 0207.

-Highlighted in  ChemistryViews

-Featured in the January edition of “Some Items of Interest to Process R&D Chemists and Engineers Org. Process Res. Dev. 2024, 28, 1, 1–10


67

Cu/Pd-catalyzed arylboration of a 1-silyl-1,3-cyclohexadiene for stereocontrolled and diverse cyclohexane/ene synthesis

Phillip F. Crook, Alan R. Lear, Suman Das and M. Kevin Brown

Chem. Sci., 2023, 14, 10467-10470.

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66

Lewis Acid Promoted [2+2] Cycloadditions of Allenes and Ketenes: Versatile Methods for Natural Product Synthesis

Renyu Guo and M. Kevin Brown

Acc. Chem. Res. 2023, 56, 2253−2264

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65

2,5-disubstituted bicyclo[2.1.1]hexanes as rigidified cyclopentane variants

.

Chem. Sci., 2023, 14, 8070-8075

Department of Chemistry, Indiana University, Bloomington, IN

SpiroChem AG, Basel, Switzerland

 

image

-Featured in the September edition of “Some Items of Interest to Process R&D Chemists and Engineers”: Org. Process Res. Dev. 2023 

 


64

Photosensitized [4+2]- and [2+2]-Cycloaddition Reactions of N-Sulfonylimines

Wang Wang and M. Kevin Brown,

Angew. Chem. Int. Ed. 2023,e202305622

 

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63

Synthesis of (±)-Phyltetralin by Cu/Pd-Catalyzed Arylboration

Grace L. Trammel, Abby C. Kerlin, Christian Zachau, and M. Kevin Brown.

Synlett2023, 34, 2197-2199.image

-Special Issue in honor of Modern Boron Chemistry: 60 Years of the Matteson Reaction

 


62

Synthesis of complex bicyclic scaffolds by intermolecular photosensitized dearomative cycloadditions of activated alkenes and naphthalenes

Wang Wang, Yanyao Cai, Renyu Guo, and M. Kevin Brown.

Chem. Sci. 2022, 13, 13582-23587.

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61

Arylboration of Enecarbamates for the Synthesis of Borylated Saturated N-Heterocycles

Grace L. Trammel1, Prashansa B. Kannangara1, Dmytro Vasko2, Oleksandr Datsenko2, Pavel Mykhailiuk2,3, and M. Kevin Brown1.

Angew. Chem. Int. Ed. 2022, 61,  e202212117.

1Department of Chemistry, Indiana University, Bloomington, IN

2Enamine Ltd., Kyiv, Ukraine

3Chemistry Department, Taras Shevchenko National University of Kyiv, Kyiv, Ukraine

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60

[2]-Ladderanes as isosteres for meta-substituted aromatic rings and rigidified cyclohexanes

Rachel C. Epplin1, Shashwati Paul1, Loïc Herter2, Christophe Salome2, Erin N. Hancock1,4, Jay F. Larrow3,5, Erich W. Baum3,5, David R. Dunstan3,5, Carol Ginsburg-Moraff3, Thomas C. Fessard2, and M. Kevin Brown1.

Nat. Commun. 202213, 6056.

1Department of Chemistry, Indiana University, Bloomington, IN

2SpiroChem AG, Basel, Switzerland

3Novartis Institutes for BioMedical Research, Cambridge, MA

4Present address: Corteva Agriscience, Indianapolis, IN

5Present address: Relay Therapeutics, Cambridge, MA

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59

Boronic Ester Enabled [2 + 2]-Cycloadditions by Temporary Coordination: Synthesis of Artochamin J and Piperarborenine B

Yanyao Liu, Dongshun Ni, and M. Kevin Brown

J. Am. Chem. Soc. 2022, 144, 18790–18796.

Featured in the September edition of “Some Items of Interest to Process R&D Chemists and Engineers”:

Org. Process Res. Dev. 2023 

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58

Photochemical Dearomative Cycloadditions of Quinolines and Alkenes: Scope and Mechanism Studies

Renyu Guo,a Souvik Adak,a Peter Bellotti,b Xinfeng Gao,a W. Walker Smith,a Sam (Ngan) Le,c Jiajia Ma,b K. N. Houk,*,d Frank Glorius,*,b Shuming Chen*,c and M. Kevin Brown*,a

J. Am. Chem. Soc. 2022, 144, 17680-17691.

a Department of Chemistry, Indiana University
b Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Germany

c Department of Chemistry and Biochemistry, Oberlin College
d Department of Chemistry and Biochemistry, University of California, Los Angeles

*co-corresponding authors

 

Photochemical Dearomative Cycloadditions of Quinolines and Alkenes: Scope and Mechanism Studies


57

Stereoselective [2+2]-Cycloadditions of chiral allenic ketones and alkenes: Applications towards the synthesis of benzocyclobutenes and endiandric acids

Renyu Guo, Brittany P. Witherspoon, and M. Kevin Brown.

Tetrahedron 2022122, 132932.

 

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-Special Issue to honor Prof. John Wood as Editor in Chief of Tetrahedron


56

Strain-Release [2π + 2σ] Cycloadditions for the Synthesis of Bicyclo[2.1.1]hexanes Initiated by Energy Transfer

Renyu Guo1, Yu-Che Chang1, Loic Herter2, Christophe Salome2, Sarah E. Braley1, Thomas C. Fessard2, and M. Kevin Brown1.

J. Am. Chem. Soc. 2022, 144, 7988-7994.

1Department of Chemistry, Indiana University, Bloomington, IN

2SpiroChem AG, Basel, Switzerland

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Highlighted by SpiroChem here.

Highlighted in Synfacts: Synfacts, 2022, 18 (7), 0787.


55

Photosensitized [2+2]-Cycloadditions of Alkenylboronates and Alkenes

Yanyao Liu*1, Dongshun Ni*1, Bernard G. Stevenson2, Vikrant Tripathy1, Sarah E. Braley1, Krishnan Raghavachari1, John R. Swierk†2and M. Kevin Brown1.

Angew. Chem. Int. Ed. 2022, 61, e202200725.

1Department of Chemistry, Indiana University, Bloomington, IN

2Department of Chemistry, Binghamton University, Binghamton, NY

*These authors contributed equally to this work

Co-corresponding authors

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54

Cooperative Pd/Cu Catalysis for Alkene Arylboration: Opportunities for Divergent Reactivity

Stanna K. Dorn and M. Kevin Brown.

ACS Catal. 2022, 12, 2058-2063.

Picture2


53

Catalytic Arylboration of Spirocyclic Cyclobutenes: Rapid Access to Highly Substituted Spiro[3.n]alkanes

Amit K. Simlandy, Mao-Yun Lyu, and M. Kevin Brown ACS Catal. 2021, 11, 12815-12820.

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52

Nickel-Catalyzed Dearomative Arylboration of Indoles: Regioselective Synthesis of C2- and C3-Borylated Indolines

Grace L. Trammel, Rositha Kuniyil, Phillip F. Crook, Peng Liu*, and M. Kevin Brown* J. Am. Chem. Soc. 2021, 143, 16502-16511.

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Highlighted in Synfacts: Synfacts, 202117 (12), 1362.


51

Modular Synthesis of a Versatile Double-Allylation Reagent for Complex Diol Synthesis

Stanna K. Dorn, Annika E. Tharp, and M. Kevin Brown Angew. Chem. Int. Ed. 2021, 60, 16027-16034.

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50

Photochemical Intermolecular Dearomative Cycloaddition of Bicyclic Azaarenes with Alkenes

Jiajia Ma1,*, Shuming Chen2,*, Peter Bellotti1,*, Renyu Guo3, Felix Schäfer1, Arne Heusler1, Xiaolong Zhang1, Constantin Daniliuc1M. Kevin Brown3,, Kendall Houk2,, and Frank Glorius1,Science. 2021, 371, 1338-1345.

1Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Germany

2Department of Chemistry and Biochemistry, University of California, Los Angeles, CA

3Department of Chemistry, Indiana University, Bloomington, IN

*These authors contributed equally to this work

Co-corresponding authors

Perspective by Prof. Valerie Schmidt (UCSD): Getting excited about cycloadditions. Science. 2021371, 1313.

Open Access links:    Abstract    Reprint    Full Text

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49

Allenylidene Induced 1,2‐Metalate Rearrangement of Indole‐Boronates: Diastereoselective Access to Highly Substituted Indolines

Amit K. Simlandy and M. Kevin Brown Angew. Chem. Int. Ed. 2021, 60, 12366-12370. 

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48

Construction of Congested Csp3-Csp3 Bonds by a Formal Ni-Catalyzed Alkylboration

Amit K. Simlandy, Stephen Sardini, and M. Kevin Brown. Chem. Sci. 202112, 5517-5521image

 

Highlighted in Synfacts: Synfacts 202117 (06), 0650.


47

Three-Component Ni-Catalyzed Silylacylation of Alkenes

Dongshun Ni and M. Kevin Brown. ACS Catal. 2021, 11, 1858-1862imageimage


46

Mechanism-Based Design of an Amide-Directed Ni-Catalyzed Arylboration of Cyclopentene Derivatives

Alison L. Lambright, Yanyao Liu, Isaac A. Joyner, Kaitlyn M. Logan, and M. Kevin Brown. Org. Lett., 2021, 23, 612-616

Featured in the April edition of “Some Items of Interest to Process R&D Chemists and Engineers”: Org. Process Res. Dev. 2021, 25, 691-702.

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45

Nickel-Catalyzed Arylboration of Cyclopentene

Stephen R. Sardini and M. Kevin Brown, Org. Synth. 2020, 97, 355-367image


44

Ladderane Natural Products: From the Ground Up

Erin N. Hancock and M. Kevin Brown Chem. Eur. J., 2021, 27, 565-576


43

Enantioselective Synthesis of (+)-Hippolide J and Reevaluation of Antifungal Activity

Renyu Guo, Sarah Beattie, Damian J. Krysan, and M. Kevin Brown. Org. Lett., 2020, 22, 7743-7746image


42

Stereoselective [4+2]-Cycloaddition with Chiral Alkenylboranes

Dongshun Ni, Brittany P. Witherspoon, Hong Zhang, Chen Zhou, Prof. K. N. Houk, Prof. M. Kevin Brown. Angew. Chem. Int. Ed., 2020, 59, 11432

Selected as a Hot Paper

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41

Evolution of a Strategy for the Enantioselective Synthesis of (-)-Cajanusine

Renyu Guo, Brittany P. Witherspoon and M. Kevin Brown* J. Am. Chem. Soc., 2020, 142, 5002image


40

Lessons in Strain and Stability: An Enantioselective Synthesis of (+)-[5]-Ladderanoic Acid

Erin N. Hancock, Erin L. Kuker, Dean Tantillo, and M. Kevin Brown Angew. Chem. Int. Ed. 2020, 59, 436

Highlighted in:

Synfacts “Synfact of the month” DOI: 10.1002/anie.201910901

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39

Ni-Catalyzed 1,2-Benzylboration of 1,2-Disubstituted Unactivated Alkenes

Seewon Joung, Allison M. Bergmann,  and M. Kevin Brown Chem. Sci., 2019, 10, 10944

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38

Regioselective Arylboration of 1,3-Butadiene

Allison M. Bergmann, Stephen R. Sardini, Kevin B. Smith, and M. Kevin Brown, Isr. J. Chem.2020, 60, 394

• Special invited article to celebrate Professors Buchwald and Hartwig’s receipt of the Wolf Prize

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37

Nickel-Catalyzed Arylboration of Alkenylarenes: Synthesis of Boron-Substituted Quaternary Carbons and Regiodivergent Reactions

Liang-An Chen, Alan Lear, Pin Gao, and M. Kevin Brown, Angew. Chem. Int. Ed., 2019, 58, 10956-10960 

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36

(Hetero)arylboration of alkynes: a strategy for the synthesis of α,α-bis(hetero)arylketones

Yuan Huang, Allison Bergmann, and M. Kevin Brown, Org. Biomol. Chem. 201917, 5913-5915.

• Special invited article for Trends in Organoboron Chemistry

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35

Thioallenoates in catalytic enantioselective [2+2]-cycloadditions with unactivated alkenes

Michael L. Conner, Johannes M. Wahl, and M. Kevin Brown, Tetrahedron201924, 3265-3271

• Special issue to honor Professor Ryan Shenvi’s receipt of the Tetrahedron Young Investigator Award

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34

Ni-Catalyzed Arylboration of Unactivated Alkenes: Scope and Mechanistic Studies

Stephen R. Sardini*, Alison L. Lambright*, Grace L. Trammel, Humair H. Omer, Peng Liu, and M. Kevin Brown J. Am. Chem. Soc. 2019, 141, 9391-9400.

* These authors contributed equally to this work

Co-corresponding authors

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33

Recent Advances in the Synthesis of Gem-dimethylcyclobutane Natural Products

Erin N. Hancock, Johannes M. Wahl and M. Kevin Brown Nat. Prod. Rep., 2019, 36, 1383-1393

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32

Synthesis of Bisheteroarylalkenes by Heteroarylboration: Development and Application of a Pyridylidene-Cu Complex

Yuan Huang, and M. Kevin Brown Angew. Chem. Int. Ed. 2019, 58, 6048-6052

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31

Catalyst-Controlled 1,2- and 1,1-Arylboration of α-Alkyl Alkenylarenes.

Allison Bergmann*, Stanna Dorn*, Kevin Smith, Kaitlyn Logan, and M. Kevin Brown, Angew. Chem. Int. Ed. 2019, 58, 1719-1723

* These authors contributed equally to this work

Selected as a Hot Paper

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30

Allenoates in Enantioselective [2+2] Cycloadditions: From a Mechanistic Curiosity to a Stereospecific Transformation

Johannes M. Wahl, Michael L. Conner, and M. Kevin Brown J. Am. Chem. Soc. 2018140, 15943-15949 

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29

Nickel-Catalyzed Stereoselective Diarylation of Alkenylarenes

Pin Gao, Liang-An Chen, and M. Kevin Brown, J. Am. Chem. Soc. 2018, 140, 10653-10657

Highlighted in:

        • Synfacts DOI: 10.1055/s-0037-1611316

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28

Copper-Catalyzed Cross-Coupling of Aryl-, Primary Alkyl-, and Secondary Alkylboranes with Heteroaryl Bromides

Allison M. Bergmann, Adam M. Oldham, Wei You, and M. Kevin Brown Chem. Commun. 2018, 54, 5381-5384image


27

Copper‐Catalyzed Heteroarylboration of 1,3‐Dienes with 3‐Bromopyridines: A cine Substitution

Kevin B. Smith, Dr. Yuan Huang, and M. Kevin Brown Angew. Chem. Int. Ed. 2018, 57, 6146-6149 

 


26

Synthesis of (-)-Hebelophyllene E: An Entry to geminal Dimethyl-cyclobutanes by [2+2] Cycloaddition of Alkenes and Allenoates

Johannes M. Wahl, Michael L. Conner, and M. Kevin Brown, Angew. Chem. Int. Ed. 2018, 57, 4647-4651

image

 

Highlighted in Synfacts: Synfacts 2018, 14 (05), 0453.


25

Nickel-Catalyzed Stereoselective Arylboration of Unactivated Alkenes

Kaitlyn M. Logan, Stephen R. Sardini, Sean D. White, and M. Kevin Brown, J. Am. Chem. Soc. 2018, 140, 159-162

        Highlighted in:

        • Synfacts DOI: 10.1055/s-0037-1609287

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24

Synthesis of ent-[3]-Ladderanol: Development and Application of Intramolecular Chirality Transfer [2+2] Cycloadditions of Allenic Ketones and Alkenes

Nathan Line*, Brittany Witherspoon*, Erin Hancock and M. Kevin Brown, J. Am. Chem. Soc,.2017, 139, 14392

      * These authors contributed equally to this work

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23

Cu-Catalyzed Borylacylation of Activated Alkenes with Acid Chlorides

Yuan Huang, Kevin Smith, and M. Kevin Brown, Angew. Chem. Int. Ed., 2017, 56, 13314

        Highlighted in:

        • Synfacts DOI: 10.1055/s-0036-1591657

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22

Catalyst Controlled Regiodivergent Arylboration of Dienes

Stephen R. Sardini and M. Kevin Brown, J. Am. Chem. Soc. 2017, 139, 9823


21

Intramolecular Chirality Transfer [2 + 2] Cycloadditions of Allenoates and Alkenes

Yao Xu, Young J. Hong, Dean J. Tantillo, and M. Kevin Brown, Org. Lett. 201719, 3703


20

Regioselective Arylboration of Isoprene and its Derivatives by Cu/Pd Cooperative Catalysis

Kevin B. Smith and M. Kevin Brown, J. Am. Chem. Soc., 2017139, 7721


19

Catalytic Enantioselective Arylboration of Alkenylarenes

Kaitlyn M. Logan and M. Kevin Brown, Angew. Chem. Int. Ed., 2017, 56, 851-855

 Highlighted in:

        • Synfacts DOI: 10.1055/s-0036-1590157

Image of Catalytic Enantioselective Arylboration of Alkenylarenes


18

Bringing Organic Chemistry to the Public: Structure and Scent in a Science Museum

M. Kevin Brown*, and Laura C. Brown*, Karen Jepson-Innes, Michael Lindeau, and Jeremy Stone J. Chem. Educ.201794, 251–255

     * These authors contributed equally to this work

Museum Image


17

Synthesis of Cyclobutanes by Lewis Acid-Promoted Ketene-Alkene [2+2] cycloaddtions

Christopher M. Rasik, Eleni Salyers, and M. Kevin Brown, Org. Synth. 2016, 93, 401

Image of Synthesis of Cyclobutanes by Lewis Acid-Promoted Ketene-Alkene [2+2] cycloaddtions


16

Synthesis of 1,3-substituted Cyclobutanes by Allenoate-Alkene [2+2] Cycloaddition

Michael L. Conner and M. Kevin Brown, J. Org. Chem., 2016, 81, 8050-8060


15

An Unexpected Lewis Acid Catalyzed Diels-Alder Cycloaddition of Aryl Allenes and Acrylates

Michael L. Conner and M. Kevin Brown, Tetrahedron, 2016, 72, 3759-3765

        • Special issue to honor Professor Neil Garg’s receipt of the Tetrahedron Young

          Investigator Award


14

Collaborative Total Synthesis: Routes to (±)-Hippolachnin A Enabled by Quadricyclane Cycloaddition and Late-Stage C-H Oxidation

Monica E. McCallum*, Christopher M. Rasik*, John L. Wood, and M. Kevin Brown, J. Am. Chem. Soc., 2016, 138, 2437-2442

        *These authors contributed equally to this work

        Co-corresponding authors

        Highlighted in:

        • C&EN: 2016, 94, 8, p. 3

        • Synfacts “Synfact of the month”: DOI: 10.1055/s-0034-1380008


13

Catalytic Enantioselective Diarylation of Alkenes

Wei You and M. Kevin Brown, J. Am. Chem. Soc., 2015, 137, 14578-14581

        Highlighted in:

        • Synfacts DOI: 10.1055/s-0035-1561165


12

Lewis Acid-Promoted [2+2] Cycloadditions of Alkenes with Arylketenes

E. M. Rigsbee, C. Zhou, C. M. Rasik, A. Z. Spitz, A. J. Nichols and M. Kevin Brown, Org. Biomol. Chem., 2016, 14, 5477-5480

            Invited article for “New Talent Issue”


11

Cyclobutane Synthesis by Catalytic Enantioselective [2+2] Cycloaddition

Yao Xu and Michael L. Conner and M. Kevin Brown, Angew. Chem. Int. Ed. 2015, 54, 11918-11928.


10

Catalytic Enantioselective Allenoate-Alkene [2+2] Cycloadditions

Michael L. Conner*, Yao Xu* and M. Kevin Brown, J. Am. Chem. Soc. 2015, 137, 3482-3485.

       * These authors contributed equally to this work

        Highlighted in:

        • Cheminform DOI: 10.1002/chin.201534090


9

Copper/Palladium Synergistic Catalysis for the syn- and anti-Selective Carboboration of Alkenes

Kaitlyn M. Logan*, Kevin B. Smith* and M. Kevin Brown,  Angew. Chem. Int. Ed. 2015, 54, 5228-5231.

      * These authors contributed equally to this work

 

Highlighted in Synfacts: Synfacts 2015 11(06), 0651.


8

Total Synthesis of Gracilioether F: Development and Application of Lewis Acid-Promoted Ketene-Alkene [2+2]-Cycloadditions and Late Stage C-H Oxidation

Christopher M. Rasik and M. Kevin Brown, Angew. Chem. Int. Ed. 2014, 53, 14522-14526


7

Diarylation of Alkenes by a Cu-Catalyzed Migratory Insertion/Cross Coupling Cascade

Wei You, and M. Kevin Brown, J. Am. Chem. Soc. 2014, 136, 14730–14733


6

Origins of Diastereoselectivity in Lewis Acid Promoted Ketene–Alkene [2 + 2] Cycloadditions

Christopher M. Rasik, Young J. Hong, Dean J. Tantillo, and M. Kevin Brown, Org. Lett. 2014, 16, 5168-5171


5

Alkene Carboboration Enabled by Synergistic Catalysis

Kevin B. Smith, Kaitlyn M. Logan, Wei You, and M. Kevin Brown, Chem. Eur. J. 2014, 20, 12032-12036


4

Copper-Catalyzed Cross-Coupling of Boronic Esters with Aryl Iodides and Application to a Carboboration of Alkynes and Allenes

Yiqing Zhou*, Wei You*, Kevin B. Smith and M. Kevin Brown, Angew. Chem. Int. Ed. 2014, 53, 3475-3479.

        * These authors contributed equally to this work

        Highlighted in:

        • Synfacts DOI: 10.1055/s-0033-1341289


3

Intermolecular Ketene-Alkene [2+2] Cycloadditions: The Significance of Lewis Acid-Promoted Variants

Christopher M. Rasik and M. Kevin Brown, Synlett. 2014, 25, 760-765.

        Invited Synpact Review


2

Stereoselective Synthesis of All-Carbon Tetrasubstituted Alkenes from In Situ Generated Ketenes and Organometallic Reagents

Wei You, Yan Li and M. Kevin Brown, Org. Lett. 2013,15, 1610–1613.

       Highlighted in:

       Synfacts “Synfact of the month” DOI: 10.1055/s-0033-1338905

       • ChemInform DOI: 10.1002/chin.201332056


1

Lewis Acid-Promoted Ketene–Alkene [2 + 2] Cycloadditions

Christopher M. Rasik and M. Kevin Brown, J. Am. Chem. Soc. 2013, 135, 1673-1676.

        Highlighted in:

        • Synfacts DOI: 10.1055/s-0032-1318470

        • ChemInform DOI: 10.1002/chin.201329050


Graduate Publications

“Sulfonate N‐Heterocyclic Carbene–Copper Complexes: Uniquely Effective Catalysts for Enantioselective Synthesis of C−C, C−B, C−H, and C−Si Bonds,” Prof. Amir H. Hoveyda, Yuebiao Zhou, Dr. Ying Shi, Prof. M. Kevin Brown, Dr. Hao Wu, and Dr. Sebastian Torker, Angew. Chem. Int. Ed. 202059, 21304-21359.

“Enantioselective Total Synthesis of Clavirolide C. Applications of Cu-Catalyzed Asymmetric Conjugate Additions and Ru-Catalyzed Ring-Closing Metathesis,” M. Kevin Brown and Amir H. Hoveyda, J. Am. Chem. Soc. 2008, 130, 12904-12906.

    •Highlighted in Nature Chemistry, September 2008

“Enantioselective Synthesis of All-Carbon Quaternary Stereogenic Centers by Catalytic Asymmetric Conjugate Additions of Alkyl and Aryl Aluminum Reagents to Five-, Six-, and Seven-Membered-Ring -Substituted Cyclic Enones,” Tricia L. May, M. Kevin Brown and Amir H. Hoveyda, Angew. Chem., Int. Ed. 2008, 47, 7358-7362.

“Highly Site- and Enantioselective Cu-Catalyzed Allylic Alkylation Reactions with Easily Accessible Vinylaluminum Reagents,” Yunmi Lee, Katsuhiro Akiyama, Dennis G. Gillingham, M. Kevin Brown and Amir H. Hoveyda, J. Am. Chem. Soc. 2008, 130, 446-447.

“All-Carbon Quaternary Stereogenic Centers by Enantioselective Cu-Catalyzed Conjugate Additions Promoted by a Chiral N-Heterocyclic Carbene,” M. Kevin Brown, Tricia L. May, Carl A. Baxter and Amir H. Hoveyda Angew. Chem., Int. Ed. 2007, 46, 1097–1110.

“A Practical Method for Enantioselective Synthesis of All-Carbon Quaternary Stereogenic Centers through NHC-Cu-Catalyzed Conjugate Additions of Alkyl- and Arylzinc Reagents to b-Substituted Cyclic Enones,” Kang-sang Lee, M. Kevin Brown, Alexander W. Hird and Amir H. Hoveyda J. Am. Chem. Soc. 2006, 128, 7182–7184.

“Highly Enantioselective Cu-Catalyzed Conjugate Additions of Dialkylzinc Reagents to Unsaturated Furanones and Pyranones.  Preparation of Air Stable and Catalytically Active Cu-Peptide Complexes,” M. Kevin Brown, Sylvia J. Degrado and Amir H. Hoveyda Angew. Chem., Int. Ed. 2005, 44, 5306–5310.


Post-Doctoral Publications

“Mechanism of the Enantioselective Oxidation of Racemic Secondary Alcohols Catalyzed by Chiral Mn(III)-Salen Complexes,” M. Kevin Brown, Megan M. Blewett, James R. Colombe and E. J. Corey, J. Am. Chem. Soc. 2010, 132, 11165-11170.

“Catalytic Enantioselective Formation of Chiral-Bridged Dienes Which Are Themselves Ligands for Enantioselective Catalysis,” M. Kevin Brown and E. J. Corey, Org. Lett. 2010, 11, 172-175

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