title: Rhenium-catalyzed regio- and stereoselective addition of imines to terminal alkynes leading to N-alkylideneallylamines.
abstract: The reaction of terminal alkynes with imines using ReBr(CO)(5) as a catalyst results in the production of N-alkylideneallylamines and not the conventional propargylamines. The substituent on the imine nitrogen is important, and a diphenylmethyl group gave the best result. The catalytic cycle of this regioselective C-C bond forming reaction appears to involve the formation of an alkynyl rhenium species and subsequent nucleophilic attack of the alkynyl β-carbon atom on the imine carbon to give a vinylidene rhenium species.
authors.affiliation: Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan. fukumoto@chem.eng.osaka-u.ac.jp
authors.forename: Yoshiya
authors.initials: Y
authors.lastname: Fukumoto
authors.forename: Masato
authors.initials: M
authors.lastname: Daijo
authors.forename: Naoto
authors.initials: N
authors.lastname: Chatani