N-Heterocyclic carbene catalysed redox isomerisation of esters to functionalised benzaldehydes

被引：77
作者：
Candish, Lisa [1 ]
Levens, Alison [1 ]
Lupton, David W. [1 ]
机构：
[1] Monash Univ, Sch Chem, Clayton, Vic 3800, Australia
来源：
CHEMICAL SCIENCE | 2015年 / 6卷 / 04期
基金：
澳大利亚研究理事会;
关键词：
ALPHA; BETA-UNSATURATED ENOL ESTERS; ENANTIOSELECTIVE SYNTHESIS; GAMMA-BUTYROLACTONES; ORGANOCATALYTIC ACTIVATION; STEREOSELECTIVE-SYNTHESIS; NUCLEOPHILIC CARBENES; CONJUGATE UMPOLUNG; DIRECT ANNULATIONS; DOMINO REACTIONS; ACYL AZOLIUMS;
D O I：
10.1039/c4sc03726j
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
N-Heterocyclic carbene catalysed redox isomerisation with reduction about the carbonyl has been developed in the transformation of trienyl esters to tetrasubstituted benzaldehydes. The reaction proceeds in good to excellent yield, and in cases that provide 2,2'-biaryls, enantioselectivity is observed. Mechanistic studies demonstrate the intermediacy of a cyclohexenyl beta-lactone, while implicating formation of the homoenolate as turnover limiting.
引用
收藏
页码：2366 / 2370
页数：5
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