Organic Letters
Organic Letters
5 years ago

Construction of Distant Stereocenters by Enantioselective Desymmetrizing Carbonyl–Ene Reaction

Construction of Distant Stereocenters by Enantioselective Desymmetrizing Carbonyl–Ene Reaction
Lili Lin, Xiaohua Liu, Xiaoming Feng, Yu Zhang, Weiwei Luo
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01329

DOI: 10.1021/acs.orglett.7b01329

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