Stereoselective Lewis Acid Mediated (3+ 2) Cycloadditions of N??H??and N??Sulfonylaziridines with Heterocumulenes

RA Craig, NR O'Connor, AFG Goldberg…

Index: Craig, Robert A.; O'Connor, Nicholas R.; Goldberg, Alexander F. G.; Stoltz, Brian M. Chemistry - A European Journal, 2014 , vol. 20, # 16 p. 4806 - 4813

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Citation Number: 24

Abstract

Abstract Alkyl and aryl isothiocyanates and carbodiimides are effective substrates in (3+ 2) cycloadditions with N-sulfonyl-2-substituted aziridines and 2-phenylaziridine for the synthesis of iminothiazolidines and iminoimidazolidines. Additionally, the stereoselective (3+ 2) cycloaddition of NH-and N-sulfonylaziridines with isothiocyanates can be accomplished, allowing for the synthesis of highly enantioenriched iminothiazolidines. ...