Practical modifications and applications of the sharpless asymmetric aminohydroxylation in the one-pot preparation of chiral oxazolidin-2-ones

Nancy S. Barta, Daniel R. Sidler, Kara B. Somerville, Steven A. Weissman, Robert D. Larsen, Paul J. Reider

Research output: Contribution to journalArticle

46 Scopus citations

Abstract

Chiral oxazolidin-2-ones are synthetically valuable as chiral auxiliaries, and many have pharmaceutically interesting biological activity. This communication focuses on a convenient, practical one-pot preparation of chiral 4,5-disubstituted oxazolidan-2-ones in good yield with high enantioselectivities, using a modified Sharpless asymmetric aminohydroxylation of β-substituted styrene derivatives followed by base-mediated ring closure. This procedure has been demonstrated on both small and large scale, utilizing 1,3-dichloro-5,5-dimethyl hydantoin as an easily handled, commercially available substitute for tert-butyl hypochlorite.

Original languageEnglish (US)
Pages (from-to)2821-2824
Number of pages4
JournalOrganic Letters
Volume2
Issue number18
DOIs
StatePublished - Sep 7 2000
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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