Catalytic Asymmetric Intermolecular Stetter Reactions of Enolizable Aldehydes with Nitrostyrenes: Computational Study Provides Insight into the Success of the Catalyst

被引：105

作者：

DiRocco, Daniel A. ^{[2
]}

Noey, Elizabeth L. ^{[1
]}

Houk, K. N. ^{[1
]}

Rovis, Tomislav ^{[2
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

[2] Colorado State Univ, Dept Chem, Ft Collins, CO 80526 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 10期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

density functional calculations; fluorination; N-heterocyclic carbenes; organocatalysis; Stetter reaction; HETEROCYCLIC ALDEHYDES; DENSITY FUNCTIONALS; ORGANOCATALYSIS; FLUORINATION; CARBENES; ENERGIES; ENALS;

D O I：

10.1002/anie.201107597

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Fluorine helps: A fluorinated triazolium salt precatalyst has been developed that efficiently promotes the asymmetric intermolecular Stetter reaction of enolizable aldehydes and nitrostyrenes (see scheme). Trans fluorination of the catalyst architecture results in unparalleled reactivity and enantioselectivity in the desired transformation. A DFT study provides evidence of an electrostatic interaction as the source of the increased enantio-induction. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：2391 / 2394

页数：4

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