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Synfacts 2010(5): 0551-0551
DOI: 10.1055/s-0029-1219695
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
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
Further Information
Publication History
Publication Date:
22 April 2010 (online)
![](https://www.thieme-connect.de/media/synfacts/201005/lookinside/thumbnails/10.1055-s-0029-1219695-1.jpg)
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.