Tetrahedron Asymmetry p. 3293 - 3308 (1997)
Update date:2022-08-03
Topics:
Takahashi, Tamiko
Nakao, Naoki
Koizumi, Toru
Enantioface-differentiating protonation of a chiral metal enolates of α-alkylcarbonyl compounds 7 has been developed using chiral γ-hydroxyselenoxides 1 as a proton source. Reaction of zinc bromide enolates of 2-benzyl- and 2-n-propylcyclohexanones with (S(Se))-1e gave (S)-2-benzylcyclohexanone 7a and (R)-2-n-propylcyclohexanone 7c in high enantiomeric excess, respectively. Intramolecular hydrogen bonding of the selenoxide 1, chelation effects between 1 and metal enolate, and 2-exo-hydroxy-10-bornyl-framework could contribute to this asymmetric induction.
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