Synlett
DOI: 10.1055/s-0036-1590742
letter
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Palladium-Catalyzed Conjugate Addition of Arylboronic Acids to α-Substituted Cyclic Enones

Ang Gaoa, Xiu-Yan Liua, Chang-Hua Ding*a, Xue-Long Hou*a, b
  • aState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai, 200032, P. R. of China   Email: dingch@sioc.ac.cn   Email: xlhou@sioc.ac.cn
  • bShanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai, 200032, P. R. of China
The authors acknowledge financial support from the National Natural Science Foundation of China (NSFC) (21532010, 21372242, 21472214, 21421091), the Strategic Priority Research Program of the Chinese Academy of Sciences (XDB20030100), the NSFC and the Research Grants Council of Hong Kong Joint Research Scheme (21361162001), the Technology Commission of Shanghai Municipality, and the Croucher Foundation of Hong Kong.
Further Information

Publication History

Received: 22 May 2017

Accepted after revision: 05 July 2017

Publication Date:
23 August 2017 (eFirst)

This paper is dedicated to Professor Victor Snieckus on the occasion of his 80th birthday.

Abstract

A palladium-catalyzed conjugate addition of arylboronic acids to α-substituted cyclic enones was developed to give α,β-disubstituted ketones with high diastereoselectivity. Mechanistic investigation showed that the high diastereoselectivity was realized through epimerization.

Supporting Information