Enantio- and diastereoselective hetero-Diels-Alder reactions between 2-aza-3-silyloxy-1,3-butadienes and aldehydes catalyzed by chiral dirhodium(II) carboxamidates

Chem Commun (Camb). 2012 Jul 14;48(55):6969-71. doi: 10.1039/c2cc32876c. Epub 2012 Jun 7.

Abstract

The first catalytic asymmetric hetero-Diels-Alder reaction between 2-aza-3-silyloxy-1,3-butadienes and aldehydes is described. With dirhodium(II) tetrakis[N-benzene-fused-phthaloyl-(S)-piperidinonate], Rh(2)(S-BPTPI)(4), the cycloaddition reaction proceeded exclusively in an endo mode to give all-cis-substituted 1,3-oxazinan-4-ones in high yields with up to 98% ee.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Butadienes / chemistry*
  • Catalysis
  • Coordination Complexes / chemistry*
  • Oxazines / chemical synthesis
  • Oxazines / chemistry
  • Rhodium / chemistry*
  • Stereoisomerism

Substances

  • Aldehydes
  • Butadienes
  • Coordination Complexes
  • Oxazines
  • Rhodium