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An Efficient Stereoselective Synthesis of 4,5-trans-i ,5-cis-3-Oxabicyclo[3.1.0]hexan-2-ones via the Iodolactonization of Alkylidenecyclopropyl Esters.
- Source :
-
Journal of Organic Chemistry . 9/16/2005, Vol. 70 Issue 19, p7629-7633. 5p. 5 Diagrams, 3 Charts. - Publication Year :
- 2005
-
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. [ABSTRACT FROM AUTHOR]
- Subjects :
- *ESTERS
*ORGANIC compounds
*IODINE
*HEXANE
*WATER
*ORGANIC chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 70
- Issue :
- 19
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 18394981
- Full Text :
- https://doi.org/10.1021/jo050878e