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Ballweg DM, Miller RC, Gray DL, et al. Stereoselective synthesis of alpha-silylamines by the direct addition of silyl anions to activated imines. Org Lett. 2005;7(7):1403-6doi: 10.1021/ol050244u.
Ballweg, D. M., Miller, R. C., Gray, D. L., & Scheidt, K. A. (2005). Stereoselective synthesis of alpha-silylamines by the direct addition of silyl anions to activated imines. Organic letters, 7(7), 1403-6. https://doi.org/10.1021/ol050244u
Ballweg, David M, et al. "Stereoselective synthesis of alpha-silylamines by the direct addition of silyl anions to activated imines." Organic letters vol. 7,7 (2005): 1403-6. doi: https://doi.org/10.1021/ol050244u
Ballweg DM, Miller RC, Gray DL, Scheidt KA. Stereoselective synthesis of alpha-silylamines by the direct addition of silyl anions to activated imines. Org Lett. 2005 Mar 31;7(7):1403-6. doi: 10.1021/ol050244u. PMID: 15787517.
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Org Lett. 2005 Mar 31;7(7):1403-6. doi: 10.1021/ol050244u.

Stereoselective synthesis of alpha-silylamines by the direct addition of silyl anions to activated imines.

Organic letters

David M Ballweg, Rebecca C Miller, Danielle L Gray, Karl A Scheidt

Affiliations

  1. Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, USA.

PMID: 15787517 DOI: 10.1021/ol050244u

Abstract

[reaction: see text] A highly efficient stereoselective synthesis of unusual alpha-silylamines via a direct silyl anion addition reaction is reported. This approach is convergent and avoids any problematic aza-Brook shifts of the anionic intermediates. The use of enantiopure tert-butanesulfinyl imines as the electrophiles affords exceedingly high levels of diastereocontrol for the newly formed stereogenic carbon.

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