Water influences the enantioselectivity in the proline or prolinamide-catalyzed aldol addition of acetone to isatins

被引：63

作者：

Angelici, Gaetano ^{[2
]}

Correa, Rodrigo J. ^{[1
]}

Garden, Simon J. ^{[1
]}

Tomasini, Claudia ^{[2
]}

机构：

[1] Univ Fed Rio de Janeiro, Dept Quim Organ, Inst Quim, BR-21945090 Rio De Janeiro, Brazil

[2] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 07期

关键词：

DFT calculations; Isatin; Organocatalysis; Proline; Water; ASYMMETRIC ALDOL; CONVOLUTAMYDINE-A; ORGANOCATALYSIS; ALDEHYDE; KETONES; ALKALOIDS; MECHANISM;

D O I：

10.1016/j.tetlet.2008.12.007

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition of small quantities of water to the proline or prolinamide-catalyzed aldol addition of acetone to isatin can result in increased enantioselectivity. DFT B3LYP calculations with a water molecule explicitly incorporated in the aldol transition states reproduce the observed enantioselectivity. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：814 / 817

页数：4

共 53 条

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