Synfacts 2018; 14(12): 1257
DOI: 10.1055/s-0037-16110111
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Nickel-Catalyzed Enantioselective Hydroalkylation of 1,3-Dienes

Contributor(s):
Hisashi Yamamoto
,
Wataru Muramatsu
Cheng L, Li M.-M, Xiao L.-J. * Xie J.-H, Zhou Q.-L. * Nankai University, Tianjin, P. R. of China
Nickel(0)-Catalyzed Hydroalkylation of 1,3-Dienes with Simple Ketones.

J. Am. Chem. Soc. 2018;
140: 11627-11630
Further Information

Publication History

Publication Date:
19 November 2018 (online)

 

Significance

Transition-metal-catalyzed asymmetric addition of enols or enolates to unsaturated hydrocarbons remains an unanswered challenge. The authors have developed a regio- and stereoselective hydroalkylation of 1,3-dienes by nickel catalysis.


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Comment

This catalytic reaction provides a wide range of γ,δ-unsaturated ketones or esters in good yields and with high enantioselectivities. One product was easily converted into the nonsteroidal anti-inflammatory drug (R)-flobufen, which also exhibits immunomodulatory properties.


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