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Synfacts 2007(1): 0066-0066  
DOI: 10.1055/s-2006-955717
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Palladium-Catalyzed [3+2] Cycloaddition

Contributor(s): Hisashi Yamamoto, Joshua P. Abell
B. M. Trost*, J. P. Stambuli, S. M. Silverman, U. Schwörer
Stanford University, USA
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Publication History

Publication Date:
15 December 2006 (online)

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Significance

[3+2] Cycloadditions provide a cyclopentane moiety that is present in a large number of natural products. Previously the formation of stereocenters utilizing palladium-catalyzed [3+2] cycloadditions relied on a chiral auxillary due to the distal location of the phosphine ligands to the enantiodetermining bond formation. Only one other case of asymmetric palladium-catalyzed [3+2] trimethylenemethane cycloaddition has been reported with ee values of 4-78% ( A. Yama­moto et al. Tetrahedron Lett. 1989, 30, 375-378).