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Synfacts 2010(4): 0447-0447
DOI: 10.1055/s-0029-1219472
DOI: 10.1055/s-0029-1219472
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Rhodium-Catalyzed Asymmetric Reductive Cyclization of Alkynals
R. Tanaka, K. Noguchi, K. Tanaka*
Tokyo University of Agriculture and Technology, Japan
Further Information
Publication History
Publication Date:
22 March 2010 (online)

Significance
Transition-metal-catalyzed cyclizations of alkynals have been extensively studied. Nickel, rhodium, ruthenium, and titanium have been reported to catalyze reductive cyclizations of alkynals efficiently, leading to cyclic allylic alcohols with a trisubstituted alkene component. Reported here is a novel asymmetric reductive cyclization of heteroatom-linked 5-alkynals 1 with heteroatom-substituted acetaldehydes 3 using a cationic rhodium(I)/(R)-H8-BINAP complex as catalyst. The cyclic allylic ester products 2 and 4 can be obtained in good yield and excellent ee.