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铑催化的功能化环戊烷和环戊酮的高度对映选择性合成。

Rh-catalyzed highly enantioselective formation of functionalized cyclopentanes and cyclopentanones.

作者信息

Liu Fei, Liu Qiang, He Minsheng, Zhang Xumu, Lei Aiwen

机构信息

College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, P. R. China.

出版信息

Org Biomol Chem. 2007 Nov 7;5(21):3531-4. doi: 10.1039/b712396e. Epub 2007 Sep 27.

Abstract

A catalyst system, Rh(COD)Cl-BINAP-AgSbF(6), has been developed as a second-generation catalyst for the cycloisomerization of 1,6-enynes tethered by carbon chains. Cyclopentanes and cyclopentanones, which can contain functional groups, such as the 1,4-dienes, vinyl ether, aldehyde etc., were obtained from readily available starting materials in high yields and selectivities. Both regioselectivities and enantioselectivities are excellent: only 1,4-dienes were observed and in over 99% ee.

摘要

一种催化剂体系[Rh(COD)Cl]₂ - BINAP - AgSbF₆已被开发出来,作为第二代催化剂用于碳链连接的1,6 - 烯炔的环异构化反应。环戊烷和环戊酮(其中可含有如1,4 - 二烯、乙烯基醚、醛等官能团)可从易得的起始原料以高收率和高选择性得到。区域选择性和对映选择性都非常出色:仅观察到1,4 - 二烯,对映体过量值超过99%。

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