Literature DB >> 16092884

Catalytic asymmetric synthesis with rh-diene complexes: 1,4-addition of arylboronic acids to unsaturated esters.

Jean-François Paquin1, Corey R J Stephenson, Christian Defieber, Erick M Carreira.   

Abstract

A general route to enantioenriched tert-butyl 3,3-diarylpropanoates is presented. These useful building blocks are prepared via an asymmetric rhodium-catalyzed conjugate addition of arylboronic acids to unsaturated tert-butyl esters in the presence of chiral dienes as ligands. The addition of both electron-poor and electron-rich boronic acids proceeds smoothly with various enoates in 63-90% yield with high enantioselectivites (89-94% ee). [reaction: see text]

Entities:  

Year:  2005        PMID: 16092884     DOI: 10.1021/ol051533l

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


  6 in total

1.  Cobalt-mediated, enantioselective synthesis of C(2) and C(1) dienes.

Authors:  W Christopher Boyd; Mark R Crimmin; Lauren E Rosebrugh; Jennifer M Schomaker; Robert G Bergman; F Dean Toste
Journal:  J Am Chem Soc       Date:  2010-10-29       Impact factor: 15.419

2.  Anionic four-electron donor-based palladacycles as catalysts for addition reactions of arylboronic acids with alpha,beta-unsaturated ketones, aldehydes, and alpha-ketoesters.

Authors:  Ping He; Yong Lu; Cheng-Guo Dong; Qiao-Sheng Hu
Journal:  Org Lett       Date:  2007-01-18       Impact factor: 6.005

3.  Expanded substrate scope and improved reactivity of ether-forming cross-coupling reactions of organotrifluoroborates and acetals.

Authors:  Cam-Van T Vo; T Andrew Mitchell; Jeffrey W Bode
Journal:  J Am Chem Soc       Date:  2011-08-17       Impact factor: 15.419

4.  Development and Analysis of a Pd(0)-Catalyzed Enantioselective 1,1-Diarylation of Acrylates Enabled by Chiral Anion Phase Transfer.

Authors:  Eiji Yamamoto; Margaret J Hilton; Manuel Orlandi; Vaneet Saini; F Dean Toste; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2016-11-30       Impact factor: 15.419

5.  Simple chiral diene ligands provide high enantioselectivities in transition-metal-catalyzed conjugate addition reactions.

Authors:  Kazuhiro Okamoto; Tamio Hayashi; Viresh H Rawal
Journal:  Org Lett       Date:  2008-09-05       Impact factor: 6.005

6.  Rh-Catalyzed Highly Enantioselective Synthesis of Aliphatic Sulfonyl Fluorides.

Authors:  Balakrishna Moku; Wan-Yin Fang; Jing Leng; Linxian Li; Gao-Feng Zha; K P Rakesh; Hua-Li Qin
Journal:  iScience       Date:  2019-10-30
  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.