Isothiourea-mediated asymmetric O- to C-carboxyl transfer of oxazolyl carbonates: Structure-selectivity profiles and mechanistic studies

Caroline Joannesse, Craig P. Johnston, Louis C. Morrill, Philip A. Woods, Madeleine Kieffer, Tobias A. Nigst, Herbert Mayr, Tomas Lebl, Douglas Philp, Ryan A. Bragg, Andrew D. Smith*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

27 Scopus citations

Abstract

The structural motif within a series of tetrahydropyrimidine-based isothioureas necessary for generating high asymmetric induction in the asymmetric Steglich rearrangement of oxazolyl carbonates is fully explored, with crossover and dynamic 19F NMR experiments used to develop a mechanistic understanding of this transformation.

Original languageEnglish (US)
Pages (from-to)2398-2408
Number of pages11
JournalChemistry - A European Journal
Volume18
Issue number8
DOIs
StatePublished - Feb 20 2012

Keywords

  • Lewis bases
  • NMR spectroscopy
  • asymmetric catalysis
  • isothioureas
  • reaction mechanisms

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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