Stereoselective synthesis of 2-carbamoyl-2-cyanocyclopropanecarboxylates by tandem oxidative cyclization and neighboring group-assisted decarboxylation.
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.
Wang
Hua
H
Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, China.
Fan
Renhua
R
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
D002264:Carboxylic Acids; D003521:Cyclopropanes; D007462:Iodobenzenes; D000644:Quaternary Ammonium Compounds; C009405:tetrabutylammonium; C037276:iodosobenzene