Asymmetric Synthesis of Tri- and Tetrasubstituted Trifluoromethyl Dihydropyranones from α-Aroyloxyaldehydes via NHC Redox Catalysis

被引：53

作者：

Davies, Alyn T. ^{[1
]}

Pickett, Philip M. ^{[1
]}

Slawin, Alexandra M. Z. ^{[1
]}

Smith, Andrew D. ^{[1
]}

机构：

[1] Univ St Andrews, Sch Chem, EaStCHEM, St Andrews KY16 9ST, Fife, Scotland

来源：

ACS CATALYSIS | 2014年 / 4卷 / 08期

基金：

欧洲研究理事会;

关键词：

asymmetric organocatalysis; N-heterocyclic carbenes; cycloaddition; trifluoromethyl; dihydropyranones; delta-lactones; DIELS-ALDER REACTIONS; ONE-POT SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; CYCLOADDITION; KETENES; FUNCTIONALIZATION; ORGANOCATALYSIS; CONVERSION; FLUORINE; AGENTS;

D O I：

10.1021/cs500667g

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The asymmetric synthesis of tri- and tetrasubstituted trifluoromethyl dihydropyranones via an NHC-catalyzed redox process, introducing methyl, benzyl, and aryl substituents to the C(5) position, is presented. Their substrate-controlled derivatization into delta-lactones and cyclic hemiacetals containing stereogenic trifluoromethyl groups is also described.

引用

页码：2696 / 2700

页数：5

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