title: Stereoselective synthesis of 2-carbamoyl-2-cyanocyclopropanecarboxylates by tandem oxidative cyclization and neighboring group-assisted decarboxylation.
abstract: In this paper, we report 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 α,β-unsaturated malonates. This method affords the desired highly functionalized cyclopropanes in moderate to good yields and with excellent diastereoselectivities. In addition, the reaction proceeds smoothly under mild conditions and with good functional group tolerance.
authors.affiliation: Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, China.
authors.forename: Hua
authors.initials: H
authors.lastname: Wang
authors.forename: Renhua
authors.initials: R
authors.lastname: Fan
mesh_terms: D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D003653:Decarboxylation; D007462:Iodobenzenes / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D002264:Carboxylic Acids; D003521:Cyclopropanes; D007462:Iodobenzenes; D000644:Quaternary Ammonium Compounds; C009405:tetrabutylammonium; C037276:iodosobenzene