Synfacts 2011(7): 0746-0746  
DOI: 10.1055/s-0030-1260642
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Rhodium-Catalyzed Asymmetric Cyclizations of γ-Alkynylaldehydes

Contributor(s): Mark Lautens, Hasnain A. Malik
K. Masuda, N. Sakiyama, R. Tanaka, K. Noguchi, K. Tanaka*
Tokyo University of Agriculture and Technology, Japan
Further Information

Publication History

Publication Date:
17 June 2011 (online)

Significance

The authors report a rhodium(I)-catalyzed asymmetric cyclization of γ-alkynylaldehydes and acyl phosphonates via C-P or C-H bond cleavage with excellent enantioselectivities. Based on ligand choice, both C-H and C-P bond cleavage products can be formed exclusively in fair to good yields and generally outstanding asymmetric induction. The authors propose several mechanistic possibilities, but indicate that further studies are needed in order to elucidate the reaction mechanism.