Enantioface-differentiating protonation with chiral gamma-hydroxyselenoxides

被引：52

作者：

Takahashi, T ^{[1
]}

Nakao, N ^{[1
]}

Koizumi, T ^{[1
]}

机构：

[1] TOYAMA MED & PHARMACEUT UNIV,FAC PHARMACEUT SCI,TOYAMA 93001,JAPAN

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 19期

关键词：

D O I：

10.1016/S0957-4166(97)00423-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Enantioface-differentiating protonation of achiral metal enolates of alpha-alkylcarbonyl compounds 7 has been developed using chiral gamma-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 7e 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. (C) 1997 Elsevier Science. Ltd.

引用

页码：3293 / 3308

页数：16

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