Gold(III) (CΛN) complex-catalyzed synthesis of propargylamines via a three-component coupling reaction of aldehydes, amines and alkynes

Propargylamines are synthesized in high yields via a gold(III) ((CN)-N-Lambda) complex-catalyzed three-component coupling reaction of aldehydes, amines and alkynes in water at 40 degrees C. Excellent diastereoselectivities (up to 99: 1) have been achieved when chiral prolinol derivatives are employed as the amine component. Notably, the [Au((CN)-N-Lambda)Cl-2] complex ((NCH)-C-Lambda = 2-phenylpyridine) could be repeatedly used for 10 reaction cycles, leading to an overall turnover number of 812. (C) 2008 Elsevier B.V. All rights reserved.