Cu(I)-catalyzed asymmetric allylation of ketones and ketimines-Reference-Cited by-同舟云学术

Cu(I)-catalyzed asymmetric allylation of ketones and ketimines

Published:2008-01-01 Issue:5 Volume:80 Page:1055-1062
ISSN:1365-3075
Container-title:Pure and Applied Chemistry
language:
Short-container-title:

Author:

Kanai Motomu¹,Wada Reiko¹,Shibuguchi Tomoyuki¹,Shibasaki Masakatsu¹

Affiliation:

1. 1Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

Abstract

Chiral CuF-catalyzed asymmetric allylation of ketones and ketimines is described. Nucleophile activation via transmetallation (allylboronate to allylcopper), which is facilitated by a cocatalyst [La(OiPr)3 or LiOiPr], is key for these reactions. A CuOTf-3KOtBu-DUPHOS complex is a comparably effective catalyst that reduces the required amount of chiral phosphines.

Publisher

Walter de Gruyter GmbH

Subject

General Chemical Engineering,General Chemistry

Link

https://www.degruyter.com/document/doi/10.1351/pac200880051055/pdf

Reference8 articles.

1. For an organo - catalytic asymmetric allylation of ketones see Pure and - catalyzed asymmetric allylation Scheme CuOtBu - catalyzed enantioselective allylation of ketones and ketimines;Lou;Am Chem Soc Applied Chemistry,2006

2. For representative reviews see Synthesis;Yamamoto;Chem Rev Chem Rev,1993

3. Although CuOtBu is an isolable solid it is extremely sensitive to air and moisture which ham - pers its routine use in organic synthesis For the preparation of CuOtBu see;Tsuda;Am Chem Soc,1972

4. For a catalytic asymmetric allylation of ketones using allylboronates see;Wada;Am Chem Soc,2004

5. AgF - catalyzed allylation of aromatic aldehydes is significantly faster than that of aliphatic alde - hydes See;Yanagisawa;Angew Chem,1999

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