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
- 19 August 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 70 (19) , 7629-7633
- https://doi.org/10.1021/jo050878e
Abstract
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.Keywords
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