Tetrahedron: Asymmetry

Enantioface-differentiating protonation with chiral γ-hydroxyselenoxides

T Takahashi, N Nakao, T Koizumi

文献索引：Takahashi, Tamiko; Nakao, Naoki; Koizumi, Toru Tetrahedron Asymmetry, 1997 , vol. 8, # 19 p. 3293 - 3308

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被引用次数: 48

摘要

Enantioface-differentiating protonation of achiral 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, ...