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

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

We developed a highly regioselective addition of 1,3-dienes with simple ketones by nickel-hydride catalyst bearing DTBM-SegPhos ligand. A wide range of aromatic and aliphatic ketones directly coupled with 1,3-dienes, providing synthetically useful γ,δ-unsaturated ketones in high yield and regioselec...

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Bibliographic Details
Published in:Journal of the American Chemical Society Vol. 140; no. 37; pp. 11627 - 11630
Main Authors: Cheng, Lei, Li, Ming-Ming, Xiao, Li-Jun, Xie, Jian-Hua, Zhou, Qi-Lin
Format: Journal Article
Language:English
Published: United States American Chemical Society 19-09-2018
Online Access:Get full text
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Summary:We developed a highly regioselective addition of 1,3-dienes with simple ketones by nickel-hydride catalyst bearing DTBM-SegPhos ligand. A wide range of aromatic and aliphatic ketones directly coupled with 1,3-dienes, providing synthetically useful γ,δ-unsaturated ketones in high yield and regioselectivity. The asymmetric version of the reaction was also realized in high enantioselectivity by using novel chiral ligand DTBM-HO-BIPHEP. The utility of this hydroalkylation was demonstrated by facile product modification and enantioselective synthesis of (R)-flobufen.
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.8b09346