SuperQuat 5,5-dimethyl-4-iso-propyloxazolidin-2-one as a mimic of Evans 4-tert-butyloxazolidin-2-one

Steven D. Bull, Stephen G. Davies, A. Christopher Garner, Dennis Kruchinin, Min-Suk Key, Paul M. Roberts, Edward D. Savory, Andrew D. Smith, James E. Thomson

Research output: Contribution to journalArticlepeer-review

55 Citations (Scopus)

Abstract

The incorporation of a gem-dimethyl group at the 5-position of a chiral oxazolidinone biases the conformation of the adjacent C(4)-stereodirecting group such that the gem-dimethyl-4-iso-propyl combination mimics a C(4)-tert-butyl group, providing higher levels of stereocontrol than a simple 4-iso-propyloxazolidinone. The generality of this principle is demonstrated with applications in stereoselective enolate alkylations, kinetic resolutions, Diels-Alder cycloadditions and Pd-catalysed asymmetric acetalisation reactions.

Original languageEnglish
Pages (from-to)2945-2964
Number of pages20
JournalOrganic & Biomolecular Chemistry
Volume4
Issue number15
DOIs
Publication statusPublished - 7 Aug 2006

Keywords

  • CARBOXYLIC-ACID DERIVATIVES
  • ASYMMETRIC-SYNTHESIS
  • CHIRAL AUXILIARIES
  • ENANTIOSELECTIVE SYNTHESIS
  • KINETIC RESOLUTION
  • 4-ISOPROPYL-5,5-DIPHENYLOXAZOLIDIN-2-ONE DIOZ
  • SECONDARY ALCOHOLS
  • ACYLATING AGENTS
  • AMINO-ACIDS
  • N-ACYLATION

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