NHC-Catalyzed Ring Expansion of Oxacycloalkane-2-carboxaldehydes: A Versatile Synthesis of Lactones

被引：62
作者：
Wang, Li [1 ]
Thai, Karen [1 ]
Gravel, Michel [1 ]
机构：
[1] Univ Saskatchewan, Dept Chem, Saskatoon, SK S7N 5C9, Canada
来源：
ORGANIC LETTERS | 2009年 / 11卷 / 04期
基金：
加拿大创新基金会; 加拿大自然科学与工程研究理事会;
关键词：
N-HETEROCYCLIC CARBENES; ALPHA; BETA-UNSATURATED ALDEHYDES; ACTIVATED CARBOXYLATES; NUCLEOPHILIC CARBENES; DERIVATIVES; PROTONATION; GENERATION; CONVERSION; COUMARINS; ALCOHOLS;
D O I：
10.1021/ol8029005
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Imidazolinium-derived carbenes catalyze the ring-expansion lactonization of oxacycloalkane-2-carboxaldehydes. A variety of functionalized five-, six-, and seven-membered lactones can be formed efficiently under mild reaction conditions. The success of this new method for the construction of lactones is highly influenced by the electronic nature of the carbene catalyst.
引用
收藏
页码：891 / 893
页数：3
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