The first catalytic enantioselective Diels-Alder reactions of 1,2-dihydropyridine: Efficient syntheses of optically active 2-azabicyclo[2.2.2]octanes with chiral BINAM derived Cr(III) salen complexes

Norito Takenaka, Yong Huang, Viresh H. Rawal

Research output: Contribution to journalArticle

78 Scopus citations

Abstract

We have synthesized a new family of enantiomerically enriched BINAM-derived Schiff base Cr(III) complexes and evaluated them as catalysts for Diels-Alder reactions. These complexes effectively catalyze, for the first time, the enantioselective Diels-Alder reactions between 1,2-dihydropyridine and N-acryloyloxazolidinone to afford 2-azabicyclo[2.2.2]octanes in high yields (89-99%) and with moderate to good enantioselectivities (79-85%).

Original languageEnglish (US)
Pages (from-to)8299-8305
Number of pages7
JournalTetrahedron
Volume58
Issue number41
DOIs
StatePublished - Oct 7 2002

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Keywords

  • 2-azabicyclo[2.2.2]octane
  • Alkaloids
  • Asymmetric catalysis
  • Diels-Alder reaction
  • Enantioselective

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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