高度对映选择性和非对映选择性催化分子间乙醛酸酯-烯反应：烯烃几何异构体的影响。

Highly enantioselective and anti-diastereoselective catalytic intermolecular glyoxylate-ene reactions: effect of the geometrical isomers of alkenes.

作者信息

Zhang Xiang, Wang Min, Ding Ran, Xu Yun-He, Loh Teck-Peng

机构信息

†Department of Chemistry, University of Science and Technology of China, Hefei 230026, China.

‡Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371.

出版信息

Org Lett. 2015 Jun 5;17(11):2736-9. doi: 10.1021/acs.orglett.5b01151. Epub 2015 May 12.

DOI:10.1021/acs.orglett.5b01151

PMID:25965690

Abstract

An efficient method for the synthesis of homoallylic alcohols with high enantioselectivities and anti-diastereoselectivities via an In(III)-catalyzed intermolecular glyoxylate-ene reaction has been developed. The geometrical isomers of alkenes were shown to have different reactivities. Only the isomers of the alkenes having a proton β-cis to the substituent reacted in this catalytic system.

摘要

已经开发出一种通过铟（III）催化的分子间乙醛酸酯-烯反应高效合成具有高对映选择性和非对映选择性的高烯丙醇的方法。结果表明，烯烃的几何异构体具有不同的反应活性。在该催化体系中，只有那些质子β-位与取代基处于顺式的烯烃异构体发生反应。