Organic Chemistry Portal

Abstracts

Search:

Copper-Catalyzed Asymmetric Reductive Allylation of Ketones with 1,3-Dienes

Bin Fu, Xiuping Yuan, Yanfei Li, Ying Wang, Qian Zhang, Tao Xiong*, Qian Zhang

*Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University, Changchun 130024, China, Email: xiongt626nenu.edu.cn

B. Fu, X. Yuan, Y. Li, Y. Wang, Q. Zhang, T. Xiong, Q. Zhang, Org. Lett., 2019, 21, 3576-3580.

DOI: 10.1021/acs.orglett.9b00979 (free Supporting Information)



see article for more reactions

Abstract

(R,R)-Ph-BPE ligated Cu catalyzes a chemo-, regio-, and enantioselective allylation of ketones with 1,3-dienes in the presence a hydrosilane to provide chiral homoallylic tertiary alcohols under very mild conditions with good functional group tolerance. 1,3-dienes as the latent allylic nucleophiles avoid the the use of stoichiometric quantities of allylmetal reagents.

see article for more examples


proposed mechanism



Key Words

homoallylic alcohols, dimethoxy(methyl)silane, CuH


ID: J54-Y2019