Literature DB >> 15957936

Catalytic enantioselective allylation of ketones via a chiral indium(III) complex.

Yong-Chua Teo1, Joshua-Daniel Goh, Teck-Peng Loh.   

Abstract

[reaction: see text] A chiral indium complex has been discovered to effect high enantioselectivities in the addition of allyltributylstannanes to ketones. The allylation of a variety of aromatic, alpha,beta-unsaturated and aliphatic ketones resulted in good yields and high enantioselectivities (up to 92% ee).

Entities:  

Year:  2005        PMID： 15957936     DOI： 10.1021/ol051018n

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


  11 in total

1.  A green chemistry approach to asymmetric catalysis: solvent-free and highly concentrated reactions.

Authors:  Patrick J Walsh; Hongmei Li; Cecilia Anaya de Parrodi
Journal:  Chem Rev       Date:  2007-05-27       Impact factor: 60.622

2.  Chiral imine copper chloride-catalyzed enantioselective desymmetrization of 2-substituted 1,2,3-propanetriols.

Authors:  Byunghyuck Jung; Sung Ho Kang
Journal:  Proc Natl Acad Sci U S A       Date:  2007-01-22       Impact factor: 11.205

3.  Highly concentrated catalytic asymmetric allylation of ketones.

Authors:  Alfred J Wooten; Jeung Gon Kim; Patrick J Walsh
Journal:  Org Lett       Date:  2007-02-01       Impact factor: 6.005

4.  Catalytic asymmetric methallylation of ketones with an (H8-BINOLate)Ti-based catalyst.

Authors:  Jeung Gon Kim; Elizabeth H Camp; Patrick J Walsh
Journal:  Org Lett       Date:  2006-09-28       Impact factor: 6.005

5.  Total Syntheses and Biological Evaluation of Both Enantiomers of Several Hydroxylated Dimeric Nuphar Alkaloids.

Authors:  Alexander Korotkov; Hui Li; Charles W Chapman; Haoran Xue; John B MacMillan; Alan Eastman; Jimmy Wu
Journal:  Angew Chem Int Ed Engl       Date:  2015-07-16       Impact factor: 15.336

6.  Allyl transfer to aldehydes and ketones by Brønsted acid activation of allyl and crotyl 1,3,2-dioxazaborolidines.

Authors:  Maureen K Reilly; Scott D Rychnovsky
Journal:  Org Lett       Date:  2010-11-05       Impact factor: 6.005

7.  A Regio- and Enantioselective CuH-Catalyzed Ketone Allylation with Terminal Allenes.

Authors:  Erica Y Tsai; Richard Y Liu; Yang Yang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2018-02-02       Impact factor: 15.419

8.  The mechanism and an improved asymmetric allylboration of ketones catalyzed by chiral biphenols.

Authors:  David S Barnett; Philip N Moquist; Scott E Schaus
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

9.  Enantioselective Allylation Using Allene, a Petroleum Cracking Byproduct.

Authors:  Richard Y Liu; Yujing Zhou; Yang Yang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2019-02-01       Impact factor: 15.419

10.  Development of a Strategy for Linear-Selective Cu-Catalyzed Reductive Coupling of Ketones and Allenes for the Synthesis of Chiral γ-Hydroxyaldehyde Equivalents.

Authors:  Raphael K Klake; Samantha L Gargaro; Skyler L Gentry; Sharon O Elele; Joshua D Sieber
Journal:  Org Lett       Date:  2019-09-18       Impact factor: 6.005
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