Asymmetric assembly of α-alkyl-α-aminosilanes using the Davis sulfinimine

ORGN 663

Yingjian Bo, and Scott McN. Sieburth, Department of Chemistry, Temple University, 1901 N. 13th Street, Philadelphia, PA 19122
In a recent report, Nielsen and Skrydstrup (J. Amer. Chem. Soc. 2008, 130, 13145.) demonstrated that addition of a silyllithium reagent to the Ellman sulfinimine (1, R = t-Bu) yields the α-amino silane 3 with excellent diastereoselectivity. This efficient approach to these structures has been studied with both Ellman and Davis (R = p-MePh) sulfinimines in the context of silanediol protease inhibitor synthesis.


Heterocycles and Aromatics, Asymmetric Reactions and Syntheses and Total Synthesis of Complex Molecules
7:00 PM-9:00 PM, Wednesday, August 19, 2009 Walter E. Washington Convention Center -- Ballroom C, Poster

8:00 PM-10:00 PM, Monday, August 17, 2009 Walter E. Washington Convention Center -- Hall D, Sci-Mix

Division of Organic Chemistry

The 238th ACS National Meeting, Washington, DC, August 16-20, 2009