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Nickel(0)-Catalyzed Hydroalkylation of 1,3-Dienes with Simple Ketones

Lei Cheng, Ming-Ming Li, Li-Jun Xiao*, Jian-Hua Xie, Qi-Lin Zhou*

*College of Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, China, Email: 1120140207mail.nankai.edu.cn, qlzhounankai.edu.cn

L. Cheng, M.-M. Li, L.-J. Xiao, J.-H. Xie, Q.-L. Zhou, J. Am. Chem. Soc., 2018, 140, 11627-11630.

DOI: 10.1021/jacs.8b09346


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Abstract

A highly regioselective addition of 1,3-dienes to simple ketones in the presence of a nickel-hydride catalyst bearing a DTBM-SegPhos ligand provides synthetically useful γ,δ-unsaturated ketones in high yield and regioselectivity. An asymmetric version of the reaction was also realized in high enantioselectivity by using (S)-DTBM-HO-BIPHEP as chiral ligand.


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Key Words

allylation of carbonyl compounds


ID: J48-Y2018