Organocatalytic Enantioselective Olefin Aminofluorination

被引：91

作者：

Appayee, Chandrakumar ^{[1
]}

Brenner-Moyer, Stacey E. ^{[1
]}

机构：

[1] CUNY Brooklyn Coll, Dept Chem, Brooklyn, NY 11210 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 15期

基金：

美国国家卫生研究院;

关键词：

ASYMMETRIC MANNICH REACTION; ALPHA; BETA-UNSATURATED ALDEHYDES; CONJUGATE ADDITION; AMINO-ACID; FLUORINATION; CATALYSIS;

D O I：

10.1021/ol101167z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral beta-fluoroamines are increasingly prevalent in medicinal compounds, but there are few efficient methods to access them from achiral starting materials. To address this, a multicomponent organocascade reaction was developed In which chiral alpha-fluoro-beta-amino aldehydes were generated in a single flask from achiral alpha,beta-unsaturated aldehydes (2), using catalyst 12a. Conversions up to 85%, dr's up to 98:2 and ee's up to 99% of the corresponding alcohol (9) were achieved in this reaction.

引用

页码：3356 / 3359

页数：4

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