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Synfacts 2006(11): 1141-1141
DOI: 10.1055/s-2006-949446
DOI: 10.1055/s-2006-949446
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
3-Component Couplings of α-Oxyaldehydes, Alkynes, and Amines in Water
B. Huang, X. Yao, C.-J. Li*
Beijing University of Chemical Technology, P. R. of China and McGill University, Montreal, Canada
Further Information
Publication History
Publication Date:
24 October 2006 (online)
Significance
The authors describe their A3-coupling (aldehyde-alkyne-amine coupling) as an attractive method for the synthesis of α-oxyamines. When α-oxyaldehydes were used, only Au(III) and Au(I) catalysts gave the desired three-component coupling product. The use of Ag(I) catalysts with the α-benzoxyaldehydes resulted in cleavage of the benzyl group and Cu catalysts gave no activity. Under AuI catalysis, α-benzyloxy, -methoxy, and -hydroxy aldehydes were tolerated, giving reasonable diastereoselectivities.