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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
- 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.
- Subjects :
- Ammonium chloride -- Chemical properties
Ammonium compounds -- Chemical properties
Ammonium paratungstate -- Chemical properties
Benzene -- Structure
Benzene -- Chemical properties
Carboxylation -- Analysis
Cyclopropane compounds -- Structure
Cyclopropane compounds -- Chemical properties
Iodine -- Chemical properties
Oxidation-reduction reaction -- Analysis
Biological sciences
Chemistry
Subjects
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