Synthesis 2017; 49(01): 159-166
DOI: 10.1055/s-0035-1562620
paper
© Georg Thieme Verlag Stuttgart · New York

Kinetic Resolution of 5-Substituted Cyclohexenols by Palladium-Catalyzed Asymmetric Redox-Relay Heck Reaction

Hao Li
a   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   eMail: dingch@sioc.ac.cn   eMail: xlhou@sioc.ac.cn
,
Ang Gao
a   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   eMail: dingch@sioc.ac.cn   eMail: xlhou@sioc.ac.cn
,
Xiu-Yan Liu
a   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   eMail: dingch@sioc.ac.cn   eMail: xlhou@sioc.ac.cn
,
Chang-Hua Ding*
a   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   eMail: dingch@sioc.ac.cn   eMail: xlhou@sioc.ac.cn
,
Bin Xu*
b   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai, 200444, P. R. of China   eMail: xubin@shu.edu.cn
,
Xue-Long Hou*
a   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   eMail: dingch@sioc.ac.cn   eMail: xlhou@sioc.ac.cn
c   Shanghai–Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China
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Publikationsverlauf

Received: 15. Juli 2016

Accepted: 22. Juli 2016

Publikationsdatum:
09. September 2016 (online)


This paper is dedicated to Professor Dieter Enders

Abstract

The kinetic resolution of 2-substituted-cyclohexenols via palladium-catalyzed asymmetric redox-relay Heck reaction was realized, providing optically active 2-substituted cyclohexenols and trans-3,5-disubstituted cyclohexan-1-ones in high yield and good enantioselectivities with an S factor up to 22.

Supporting Information