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Synfacts 2006(8): 0814-0814  
DOI: 10.1055/s-2006-942012
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Alkylation of α,β-Unsaturated Imines via C-H Bond Activation

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
D. A. Colby, R. G. Bergman*, J. A. Ellman*
University of California, Berkeley, USA
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Publikationsverlauf

Publikationsdatum:
21. Juli 2006 (online)

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Significance

Alkylation of α,β-unsaturated imines is achieved through C-H bond activation. The N-benzyl imines were alkylated with various terminal alkenes (one example with a terminal alkyne) and very high Z/E ratios were obtained (>95:5 Z/E) for the imine product. Hydrolysis to the aldehyde often resulted in isomerization of the olefin. A mild hydrolysis protocol using activity III neutral alumina was developed to provide the aldehyde with a high integrity of retention of stereochemistry.