American Chemical Society
ol7b01329_si_002.cif (310.4 kB)

Construction of Distant Stereocenters by Enantioselective Desymmetrizing Carbonyl–Ene Reaction

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posted on 2017-06-14, 13:46 authored by Weiwei Luo, Lili Lin, Yu Zhang, Xiaohua Liu, Xiaoming Feng
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.