Literature DB >> 23157440

A general method for the enantioselective synthesis of α-chiral heterocycles.

Phong Q Le1, Thien S Nguyen, Jeremy A May.   

Abstract

The enantioselective formation of stereocenters proximal to unprotected heterocycles has been accomplished. Thus, vinyl boronic acids are added to heterocycle-appended enones via a modified-BINOL catalyst. Catalyst design was key to enable a general reaction. High yields and useful er's are observed for a host of common heteroaryls.

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Year:  2012        PMID： 23157440     DOI： 10.1021/ol3030605

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.  Synthesis and evaluation of 1,7-diheteroarylhepta-1,4,6-trien-3-ones as curcumin-based anticancer agents.

Authors:  Rubing Wang; Xiaojie Zhang; Chengsheng Chen; Guanglin Chen; Qiu Zhong; Qiang Zhang; Shilong Zheng; Guangdi Wang; Qiao-Hong Chen
Journal:  Eur J Med Chem       Date:  2016-01-21       Impact factor: 6.514

3.  Boron carboxylate catalysis of homoallylboration.

Authors:  Gabrielle J Dugas; Yu-hong Lam; K N Houk; Isaac J Krauss
Journal:  J Org Chem       Date:  2014-04-24       Impact factor: 4.354

4.  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

5.  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
  5 in total

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