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Synfacts 2005(1): 0127-0127  
DOI: 10.1055/s-2005-916011
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Sequential Catalytic Asymmetric Heck-Iminium Ion Cyclization

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
A. B. Dounay, L. E. Overman*, A. D. Wrobleski
University of California, Irvine, USA
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Publication History

Publication Date:
21 September 2005 (online)

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Significance

This is a nice procedure for the construction of enantiopure (dihydroiminoethano)carbazoles, utilizing a sequential Heck-iminium ion cyclization scheme. A catalyst loading of 15 mol% Pd, and 45% equivalents of the Pfaltz ligand gave the cyclized product with 99% ee. The development of this transformation provides the first total synthesis of (+)-minfiensine.