Journal
JOURNAL OF ORGANOMETALLIC CHEMISTRY
Volume 694, Issue 4, Pages 583-591Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jorganchem.2008.12.008
Keywords
Gold(III) catalyst; Three-component coupling reaction; Propargylamines; Prolinol derivatives
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Funding
- Hong Kong Research Grants Council [PolyU 7052/07P]
- PolyU Departmental General Research Funds
- The University of Hong Kong
- University Grants Committee of the Hong Kong SAR of China [AoE/P-10/01]
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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.
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