期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 130, 期 1, 页码 46-+出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja076802c
关键词
-
资金
- NIDDK NIH HHS [DK38226, P01 DK038226, P01 DK038226-220006] Funding Source: Medline
- NIGMS NIH HHS [GM31278, R01 GM031278-24, R01 GM031278] Funding Source: Medline
An organocatalytic, enantioselective oxy-Michael addition to achiral gamma- and delta-hydroxy-alpha, beta-enones was developed. The key transformation is an unprecedented, asymmetric conjugate addition triggered by complexation between an in situ generated boronic acid hemiester and a chiral amine catalyst. Functionally, the intermediate amine-boronate complex acts as a chiral hydroxide surrogate or synthon. The resultant chiral beta-hydroxy-ketones are obtained in good to excellent yields and high ee following mild oxidative removal of the cyclic boronate. Natural products (R,12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dienyl acetate and (+)-(S)-streptenol A were synthesized to demonstrate the utility of this reaction.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据