Novel organic catalysts for the direct enantioselective α-oxidation of carbonyl compounds

被引：73

作者：

Sundén, H ^{[1
]}

Dahlin, N ^{[1
]}

Ibrahem, I ^{[1
]}

Adolfsson, H ^{[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 / 19期

关键词：

proline-derived N-sulfonylcarboxamides; asymmetric catalysis; nitroso Diels-Alder; ketones; aldehydes;

D O I：

10.1016/j.tetlet.2005.03.085

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The proline-derived N-sulfonylcarboxamide-catalyzed direct enantioselective alpha-oxidation of ketones and aldehydes with nitrosobenzene is presented. The reactions proceed smoothly furnishing the corresponding alpha-aminoxylated compounds in good yields with up to > 99% ee. The proline-derived N-sulfonylcarboxamides were also found to be excellent catalysts for the direct enantioselective nitroso Diels-Alder-type reaction between nitrosobenzene and of alpha,beta-unsaturated cyclic ketones yielding the corresponding bicyclic Diels-Alder adduct products with tip to > 99% ee. The proline-derived N-sulfonylcarboxamides represent a readily available and highly modular novel type of organic catalyst. (c) 2005 Elsevier Ltd. All rights reservesd.

引用

页码：3385 / 3389

页数：5

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