Diastereo- and enantioselective conjugate addition of alpha-ketoesters to nitroalkenes catalyzed by a chiral Ni(OAc)(2) complex under mild conditions

A highly efficient, catalytic, diastereo- and enantioselective conjugate addition of alpha-ketoesters to nitroalkenes has been devised. The reaction was applicable to various substrates. Notably, the combination of endogenous and exogenous bases was effective, allowing a small amount of the catalyst...

Full description

Saved in:
Bibliographic Details
Published in:Journal of the American Chemical Society 2010-03, Vol.132 (12), p.4036-4037
Main Authors: Nakamura, Ayako, Lectard, Sylvain, Hashizume, Daisuke, Hamashima, Yoshitaka, Sodeoka, Mikiko
Format: Article
Language:English
Subjects:
Acetates - chemistry
Alkenes - chemistry
Catalysis
Esters - chemistry
Ketones - chemistry
Molecular Structure
Nickel - chemistry
Nitro Compounds - chemistry
Stereoisomerism
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A highly efficient, catalytic, diastereo- and enantioselective conjugate addition of alpha-ketoesters to nitroalkenes has been devised. The reaction was applicable to various substrates. Notably, the combination of endogenous and exogenous bases was effective, allowing a small amount of the catalyst (0.1-1 mol % Ni) to promote the reaction efficiently. The synthetic utility of this reaction was demonstrated in the synthesis of substituted pyrrolidine derivatives, whose stereochemistry is closely related to biologically important natural products such as kainic acid.
ISSN:1520-5126
DOI:10.1021/ja909457b