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Copper(I)-Catalyzed Regioselective Asymmetric Addition of 1,4-Pentadiene to Ketones

Feng Zhong, Zhi-Zhou Pan, Si-Wei Zhou, Hai-Jun Zhang and Liang Yin*

*Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China, Email:

F. Zhong, Z.-Z. Pan, S.-W. Zhou, H.-Jun. Zhang, L. Yin, J. Am. Chem. Soc., 2021, 143, 4556-4562.

DOI: 10.1021/jacs.1c02084

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Copper(I) catalyzes a regioselective asymmetric allylation of ketones with commercially available 1,4-pentadiene as a pronucleophile to provide a variety of chiral tertiary alcohols bearing a terminal (Z)-1,3-diene in high (Z)/(E) ratio and high enantioselectivity. The synthetic utility of the product is demonstrated by a copper(I)-catalyzed regioselective borylation of the 1,3-diene group.

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Key Words

homoallylic alcohols

ID: J48-Y2021