Construction of Distant Stereocenters by Enantioselective Desymmetrizing Carbonyl–Ene Reaction

An efficient desymmetrizing carbonyl–ene reaction of 1-substituted 4-methylenecyclohexanes with glyoxal derivatives was thus executed by a chiral N,N′-dioxide/NiII catalyst, providing facile access to cyclohexene derivatives bearing two remote 1,6-related stereocenters. This distal stereocontrol met...

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Bibliographic Details
Published in:Organic letters 2017-07, Vol.19 (13), p.3374-3377
Main Authors: Luo, Weiwei, Lin, Lili, Zhang, Yu, Liu, Xiaohua, Feng, Xiaoming
Format: Article
Language:English
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Summary:An efficient desymmetrizing carbonyl–ene reaction of 1-substituted 4-methylenecyclohexanes with glyoxal derivatives was thus executed by a chiral N,N′-dioxide/NiII catalyst, providing facile access to cyclohexene derivatives bearing two remote 1,6-related stereocenters. This distal stereocontrol methodology originates from the efficient interaction between the catalyst with enophiles, discrimination of the two chair conformations of olefinic components, and the intrinsic six-membered transition-state structure of ene process.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b01329