烷基锌及官能化烷基锌试剂对酮的催化不对称加成反应。

Catalytic asymmetric addition of alkylzinc and functionalized alkylzinc reagents to ketones.

作者信息

Jeon Sang-Jin, Li Hongmei, García Celina, LaRochelle Lynne K, Walsh Patrick J

机构信息

P. Roy and Diana T. Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA.

出版信息

J Org Chem. 2005 Jan 21;70(2):448-55. doi: 10.1021/jo048683e.

DOI:10.1021/jo048683e

PMID:15651785

Abstract

We describe our full report of the catalytic asymmetric addition of simple and functionalized dialkylzinc reagents to a broad range of saturated ketones and enones. The functionalized organozinc reagents contain esters, silyl ethers, alkyl chlorides, and alkyl bromides. In general, the resulting tertiary alcohol products are isolated with high ee's. With some substrates, yields are low as a result of the formation of aldol byproducts. Most substrates undergo additions with good yields reaching as high as 91%.

摘要

我们描述了关于简单和官能化二烷基锌试剂对多种饱和酮和烯酮进行催化不对称加成的完整报告。官能化有机锌试剂包含酯、硅醚、烷基氯和烷基溴。一般来说，所得叔醇产物以高对映体过量值被分离出来。对于一些底物，由于形成了羟醛副产物，产率较低。大多数底物进行加成反应时产率良好，高达91%。