Brown Lab
Indiana University
44

Ladderane Natural Products: From the Ground Up

Erin N. Hancock and M. Kevin Brown Chem. Eur. J., 2020, ASAP


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, ASAP


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


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, 5002


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


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


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


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 


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


35

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

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

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


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


33

Recent Advances in the Synthesis of Gem-dimethylcyclobutane Natural Products

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


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


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


30

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

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


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


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, 5381-5384


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


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


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


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


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


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


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


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


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

“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