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

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

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

45 Scopus citations

Abstract

(Chemical Equation Presented) A highly efficient stereoselective synthesis of unusual α-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.

Original languageEnglish (US)
Pages (from-to)1403-1406
Number of pages4
JournalOrganic Letters
Volume7
Issue number7
DOIs
StatePublished - Mar 31 2005

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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