Stereoselective synthesis of anti-N-protected 3-amino-1,2-epoxides by nucleophilic addition to N-tert-butanesulfinyl imine of a glyceraldehyde synthon

Scott S. Harried, Michael D. Croghan, Matthew R. Kaller, Patricia Lopez, Wenge Zhong, Randall Hungate, Paul J. Reider

Research output: Contribution to journalArticle

29 Scopus citations

Abstract

(Chemical Equation Presented) A di-O-TBS protected glyceraldehyde synthon was condensed with Ellman's reagent to form a bench-stable N-tert-butanesulfinyl imine 6, which served as a common intermediate for the stereoselective introduction of various R groups. The Ellman adducts were converted to useful multifunctional intermediates 18a-i in one pot. The alcohols 18a-i were efficiently elaborated to both known and novel anti-N-protected-3-amino-1,2- epoxides in two steps. Compound 2a is a key intermediate toward HIV protease inhibitors.

Original languageEnglish (US)
Pages (from-to)5975-5982
Number of pages8
JournalJournal of Organic Chemistry
Volume74
Issue number16
DOIs
StatePublished - Jan 1 2009

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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