Asymmetric Hydrocyanation of α,β-Unsaturated Ketones into β-Cyano Ketones with the [Ru(phgly)2(binap)]/C6H5OLi Catalyst System

被引：61

作者：

Kurono, Nobuhito ^{[1
]}

Nii, Noriyuki ^{[1
]}

Sakaguchi, Yusuke ^{[1
]}

Uemura, Masato ^{[1
]}

Ohkuma, Takeshi ^{[1
]}

机构：

[1] Hokkaido Univ, Fac Engn, Div Chem Proc Engn, Sapporo, Hokkaido 0608628, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 24期

关键词：

asymmetric catalysis; hydrocyanation; lithium; ruthenium; alpha; beta-unsaturated ketones; ENANTIOSELECTIVE CONJUGATE ADDITION; CYANATION; IMIDES; ENONES;

D O I：

10.1002/anie.201100939

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantioselective conjugate addition of HCN to α,β-unsaturated ketones catalyzed by the combined system of [Ru{(S)-phgly}2{(S)- binap}] and C6H5OLi has afforded β-cyano ketones in high yield (see scheme). No detectable amount of the corresponding 1,2-adduct was produced and tert-C4H9OCH3 was the solvent of choice. The cyanation was conducted with a substrate-to-catalyst molar ratio in the range of 200:1-1000:1 at -20-0°C. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：5541 / 5544

页数：4

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