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Stereoselective synthesis of 2-carbamoyl-2-cyanocyclopropanecarboxylates by tandem oxidative cyclization and neighboring group-assisted decarboxylation

Stereoselective synthesis of 2-carbamoyl-2-cyanocyclopropanecarboxylates by tandem oxidative cyclization and neighboring group-assisted decarboxylation

Authors :
Hua Wang
Renhua Fan
Source :
Journal of Organic Chemistry. Oct 15, 2010, Vol. 75 Issue 20, 6994-6997
Publication Year :
2010

Abstract

A facile synthesis of 2-carbamoyl-2-cyanocyclopropanecarboxylates through a tandem iodosobenzene/tetrabutylammonium iodide-induced oxidative cyclization and a subsequent neighboring group-assisted decarboxylation of the Michael adducts of 2-cyanoacetamides with [alpha],[beta]-unsaturated malonates is described. The method is observed to proceed smoothly under mild conditions and with good functional group tolerance and could be used to obtain highly functionalized cyclopropanes in moderate to good yields and with excellent diastereoselectivities.

Details

Language :
English
ISSN :
00223263
Volume :
75
Issue :
20
Database :
Gale General OneFile
Journal :
Journal of Organic Chemistry
Publication Type :
Academic Journal
Accession number :
edsgcl.240054904