Literature DB >> 21846131

Enantioselective conjugate addition of alkenylboronic acids to indole-appended enones.

Brian J Lundy1, Santa Jansone-Popova, Jeremy A May.   

Abstract

An enantioselective addition of alkenylboronic acids and alkynylboronic esters to unprotected indole-appended enones is reported. This transformation proceeds with high enantioselectivity and high product yields via the use of catalytic amounts of 3,3'-bis(pentafluorophenyl)-BINOL and Mg(Ot-Bu)(2). A range of α-branched indole derivatives are available from the transformation.
© 2011 American Chemical Society

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Year:  2011        PMID: 21846131     DOI: 10.1021/ol2020847

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  5 in total

1.  Asymmetric Petasis Borono-Mannich Allylation Reactions Catalyzed by Chiral Biphenols.

Authors:  Yao Jiang; Scott E Schaus
Journal:  Angew Chem Int Ed Engl       Date:  2017-01-04       Impact factor: 15.336

2.  Enantioselective Multicomponent Condensation Reactions of Phenols, Aldehydes, and Boronates Catalyzed by Chiral Biphenols.

Authors:  Keith S Barbato; Yi Luan; Daniele Ramella; James S Panek; Scott E Schaus
Journal:  Org Lett       Date:  2015-11-18       Impact factor: 6.005

3.  Rate Dependence on Inductive and Resonance Effects for the Organocatalyzed Enantioselective Conjugate Addition of Alkenyl and Alkynyl Boronic Acids to β-Indolyl Enones and β-Pyrrolyl Enones.

Authors:  Amy Boylan; Thien S Nguyen; Brian J Lundy; Jian-Yuan Li; Ravikrishna Vallakati; Sasha Sundstrom; Jeremy A May
Journal:  Molecules       Date:  2021-03-14       Impact factor: 4.411

4.  Crown Ether-Derived Chiral BINOL: Enantioselective Michael Addition of Alkenyl Boronic Acids to α,β-Unsaturated Ketones.

Authors:  Jia-Ju Tao; Jia-Dong Tang; Tao Hong; Jia-Wen Ye; Jia-Yu Chen; Chunsong Xie; Zibin Zhang; Shijun Li
Journal:  ACS Omega       Date:  2021-12-10

Review 5.  Chiral Diol-Based Organocatalysts in Enantioselective Reactions.

Authors:  Truong N Nguyen; Po-An Chen; Krit Setthakarn; Jeremy A May
Journal:  Molecules       Date:  2018-09-11       Impact factor: 4.411

  5 in total

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