Self-assembly of an organocatalyst for the enantioselective synthesis of Michael adducts and α-aminoxy alcohols in a nonpolar medium

被引：10

作者：

Demir, Ayhan Sitki ^{[1
]}

Basceken, Sinan ^{[1
,2
]}

机构：

[1] Middle E Tech Univ, Dept Chem, TR-06531 Ankara, Turkey

[2] Hitit Univ, Dept Chem, TR-19030 Corum, Turkey

来源：

TETRAHEDRON-ASYMMETRY | 2013年 / 24卷 / 19期

关键词：

ALDEHYDES; AMINATION; AMINOOXYLATION; CATALYSTS; 1,2-DIOLS; ADDITIONS; KETONES; ROUTE;

D O I：

10.1016/j.tetasy.2013.08.008

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A proline-thiourea host-guest complex is described as a self-assembled organocatalyst for the enantioselective Michael addition of aldehydes to nitroolefins and for the asymmetric alpha-aminoxylation of both aldehydes and ketones. The Michael adducts were obtained in good yields of up to 80%, high diastereo-selectivities of up to 5:95, and high enantiomeric excesses of up to 98%. The optically active aminoxy alcohols were synthesized in 60-85% yields with 94-99% enantiomeric excesses after reduction of the alpha-oxidation products using NaBH4. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：1218 / 1224

页数：7

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