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Synfacts 2010(5): 0551-0551  
DOI: 10.1055/s-0029-1219695
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Diastereoselective Zinc-Catalyzed Propargylation of Chiral Imines

Contributor(s): Mark Lautens, Stephen G. Newman
D. R. Fandrick*, C. S. Johnson, K. R. Fandrick, J. T. Reeves, Z. Tan, H. Lee, J. J. Song, N. K. Yee, C. H. Senanayake
Boehringer Ingelheim Pharmaceuticals, Ridgefield, USA
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Publication History

Publication Date:
22 April 2010 (online)

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Significance

Enantiomerically pure sulfinyl im­ines are effective electrophiles in highly diastereoselective addition reactions (see Review below). Expanding on previous work on the synthesis of homopropargyl alcohols (D. R. Fandrick et al. Org. Lett. 2010, 12, 88), the authors present a zinc-catalyzed addition of propargyl borolanes to tert-butanesulfinyl imines.

Review: F. Ferreira et al. Chem. Soc. Rev. 2009, 38, 1162-1186.