Isothiourea-catalyzed enantioselective carboxy group transfer

Caroline Joannesse*, Craig P. Johnston, Carmen Concellón, Carmen Simal, Douglas Philp, Andrew D. Smith

*Corresponding author for this work

Research output: Contribution to journalArticle

117 Scopus citations

Abstract

Transferable skills: Enantiomerically pure isothioureas promote the 0-to C-carboxyl group transfer of oxazolyl carbonates with excellent levels of enantiocontrol (see scheme). The origin of the enantioselectivity of this process was probed mechanistically and rationalized computationally.

Original languageEnglish (US)
Pages (from-to)8914-8918
Number of pages5
JournalAngewandte Chemie - International Edition
Volume48
Issue number47
DOIs
StatePublished - Nov 9 2009

Keywords

  • Asymmetric catalysis
  • Carboxy group transfer
  • Heterocycles
  • Isothloureas, organocatalysis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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    Joannesse, C., Johnston, C. P., Concellón, C., Simal, C., Philp, D., & Smith, A. D. (2009). Isothiourea-catalyzed enantioselective carboxy group transfer. Angewandte Chemie - International Edition, 48(47), 8914-8918. https://doi.org/10.1002/anie.200904333