Enantioselective NHC-Catalyzed Redox [2+2] Cycloadditions with Perfluoroketones: A Route to Fluorinated Oxetanes

被引：24
|
作者：
Davies, Alyn T. [1 ]
Slawin, Alexandra M. Z. [1 ]
Smith, Andrew D. [1 ]
机构：
[1] Univ St Andrews North Haugh, EaStCHEM, Sch Chem, St Andrews KY16 9ST, Fife, Scotland
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2015年 / 21卷 / 52期
基金：
欧洲研究理事会; 英国工程与自然科学研究理事会;
关键词：
Lewis base; N-heterocyclic carbene; organocatalysis; oxetane; pentafluoroethyl; DIELS-ALDER REACTIONS; ASYMMETRIC-SYNTHESIS; TRIFLUOROMETHYL DIHYDROPYRANONES; ORGANOCATALYTIC ACTIVATION; ENOLATE EQUIVALENTS; ALLENOATES; ANNULATION; ALDEHYDES; ESTERS; ENALS;
D O I：
10.1002/chem.201504256
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The N-heterocyclic carbene (NHC) catalyzed redox formal [2+ 2] cycloaddition between alpha-aroyloxyaldehydes and perfluoroketones, followed by ring-opening in situ delivers a variety of perfluorinated beta-hydroxycarbonyl compounds in good yield, and excellent diastereo- and enantioselectivity. Through a reductive work-up and subsequent cyclization, this protocol offers access to highly substituted fluorinated oxetanes in two steps and in high ee.
引用
收藏
页码：18944 / 18948
页数：5
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