ASYMMETRIC α-ALKYLATION OF CYCLOHEXANONE BY MEDIATION OF A CHIRAL LIGAND AND THE LEAVING-GROUP EFFECT OF ELECTROPHILES ON ENANTIOSELECTIVITY

Kiyoshi TOMIOKA; Mitsuru SHINDO; Kenji KOGA

doi:10.1248/cpb.37.1120

Kiyoshi TOMIOKA, Mitsuru SHINDO, Kenji KOGA

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Keywords: asymmetric alkylation, chiral ligand, leaving group effect, enantioselectivity, lithioenamine

JOURNAL FREE ACCESS

1989 Volume 37 Issue 4 Pages 1120-1122

DOI https://doi.org/10.1248/cpb.37.1120

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Abstract

By the mediation of a chiral amino ether (4), the asymmetric α-benzylation of cyclohexanone (1) was effected via an achiral lithioenamine (6) to give α-benzylcyclohexanone (3) in up to 52% ee. A dramatic leaving-group effect of electrophiles on enantioselectivity was also observed.

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