Chemistry Letters p. 207 - 208 (1996)
Update date:2022-09-26
Topics:
Takahashi, Tamiko
Nakao, Naoki
Koizumi, Toru
Enantioselective protonation of a simple enolate has been developed using an optically pure γ-hydroxyselenoxide 1 as a chiral proton source. Reaction of zinc bromide enolate 7b with (Sse)-selenoxide (Sse)-1c gave (S)-2-benzylcyclohexanone (S)-8 with high enantioselectivity. Intramolecular hydrogen bonding between hydroxy group and seleninyl-oxygen of 1 would contribute to this asymmetric induction.
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