An efficient stereoselective synthesis of 4,5-trans-1,5-cis-3-oxabicyclo[3.1.0]hexan-2-ones via the iodolactonization of alkylidenecyclopropyl esters.
[reaction: see text] A highly stereoselective iodolactonization of alkylidenecyclopropyl esters with iodine or N-iodosuccinimide (NIS) in aqueous CH3CN to afford 4,5-trans-1,5-cis-3-oxabicyclo-[3.1.0]hexane-2-ones is described. The reaction is very general, accommodating a wide range of substituents. A plausible mechanism that explains the essential role of water in this reaction is proposed.
Ma
Shengming
S
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, People's Republic of China. masm@mail.sioc.ac.cn
Lu
Lianghua
L