Direct organocatalytic asymmetric α-oxidation of ketones with iodosobenzene and N-sulfonyloxaziridines

被引：46

作者：

Engqvist, M ^{[1
]}

Casas, J ^{[1
]}

Sundén, H ^{[1
]}

Ibrahem, I ^{[1
]}

Córdova, A ^{[1
]}

机构：

[1] Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 12期

关键词：

D O I：

10.1016/j.tetlet.2005.01.167

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The novel, direct amino acid-catalyzed alpha-oxidation of ketones with iodosobenzene and N-sulfonyloxaziridines is presented. A screen of several synthetically common oxidants revealed that iodosobenzene and N-sulfonyloxaziridines act as electrophiles in the direct organocatalytic asymmetric alpha-hydroxylation of ketones. The direct proline-catalyzed asymmetric alpha-oxidation of ketones with iodosobenzene yielded the corresponding alpha-hydroxylated ketones with up to 77% ee. Furthermore, several amino acid derivatives catalyze the stereoselective alpha-oxidation of ketones with N-sulfonyloxaziridines. For example, the direct diamine-catalyzed enantioselective alpha-hydroxylation of ketones with N-sulfonyloxaziridines furnished the corresponding alpha-hydroxylated products in moderate yield with up to 63% ee. (C) 2005 Elsevier Ltd. All rights reserved.

引用

页码：2053 / 2057

页数：5

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