login

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

Organic LettersPublished 22 January 2009
Li Wang, Karen Thai, Michel Gravel
Citations101
SJR quartileQ1
SJR score1.24
SNIP1.03

TL;DR

Imidazolinium-derived carbenes catalyze the ring-expansion lactonization of oxacycloalkane-2-carboxaldehydes and a variety of functionalized five-, six-, and seven-membered lactones can be formed efficiently under mild reaction conditions.

Abstract

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.

Keywords

Chemistry