Journal of the American Chemical Society

A [3+ 2] cycloaddition and [4+ 3] cycloaddition approach to N-heterocycles via palladium-catalyzed TMM reactions with imines

BM Trost, CM Marrs

Index: Trost, Barry M.; Marrs, Christopher M. Journal of the American Chemical Society, 1993 , vol. 115, # 15 p. 6636 - 6645

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Citation Number: 100

Abstract

Abstract: The question of cycloadditions of (trimethy1enemethane) palladium complexes to heteroatom unsaturation is probed in the context of pyrrolidine syntheses. Whereas simple imines fail to react, imines possessing an electronwithdrawing group at either the carbon or nitrogen enhance the electrophilicity of the imine sufficiently to make it an excellent acceptor. Palladium (0) complexes catalyze cycloadditions of 2-((trimethylsilyl) methyl) allyl esters to ...