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: xiongt626
nenu.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
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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.
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proposed mechanism
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Key Words
homoallylic alcohols, dimethoxy(methyl)silane, CuH
ID: J54-Y2019
