Remarkably low catalyst loading in brønsted acid catalyzed transfer hydrogenations: Enantioselective reduction of benzoxazines, benzothiazines, and benzoxazinones

Magnus Rueping*, Andrey P. Antonchick, Thomas Theissmann

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

258 Scopus citations

Abstract

(Chemical Equation Presented) A highly efficient transfer hydrogenation of benzoxazines, benzothiazines, and benzoxazinones with as low as 0.01 mol % binol phosphate catalyst furnishes the dihydro-2H-benzoxazines, -benzothiazines, and -benzoxazinones in good yields and with excellent enantioselectivities (see scheme). Particularly noteworthy are the mild reaction conditions and the wide scope of substrates, including sulfur-containing compounds.

Original languageEnglish (US)
Pages (from-to)6751-6755
Number of pages5
JournalAngewandte Chemie - International Edition
Volume45
Issue number40
DOIs
StatePublished - Oct 13 2006

Keywords

  • Binol phosphate
  • Brønsted acids
  • Enantioselective hydrogenation
  • Hantzsch dihydropyridine
  • Ion-pair catalysis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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