Higher enantioselectivities in thiourea-catalyzed Michael additions under solvent-free conditions

被引：32

作者：

Hestericova, Martina ^{[1
]}

Sebesta, Radovan ^{[1
]}

机构：

[1] Comenius Univ, Fac Nat Sci, Dept Organ Chem, SK-84215 Bratislava, Slovakia

来源：

TETRAHEDRON | 2014年 / 70卷 / 04期

关键词：

Asymmetric organocatalysis; Hydrogen bond; Thiourea; Michael addition; Mechanochemistry; ALDOL REACTION; ORGANOCATALYTIC REACTIONS; (S)-PROLINE-CONTAINING DIPEPTIDES; ASYMMETRIC ORGANOCATALYSIS; 1,3-DICARBONYL COMPOUNDS; CONJUGATE ADDITION; BOND DONORS; NITROALKENES; DERIVATIVES; ALDEHYDES;

D O I：

10.1016/j.tet.2013.12.029

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective Michael additions catalyzed by hydrogen-bonding catalysts produce many important compounds. Solvent-free reaction conditions in a ball mill can provide an improved enantioselectivity over the reaction in solution, due to lack of disruptive solvation of reagents. A range of 15 structurally different hydrogen-bonding organocatalysts were tested in two Michael additions to beta-nitrostyrene under solvent-free conditions and compared with corresponding experiments in solution. With several thiourea catalysts, these Michael additions proceeded with higher enantioselectivities under solvent-free conditions than in solution. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：901 / 905

页数：5

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