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Highly diastereoselective synthesis of 2-azabicyclo[2.2.1]hept-5-ene derivatives: Bronsted acid catalyzed aza-Diels–Alder reaction between cyclopentadiene and imino-acetates with two chiral auxiliaries

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
67
Issue
37
Identifiers
DOI: 10.1016/j.tet.2011.06.097
Keywords
  • Asymetric Synthesis
  • Cycloadditions
  • Aza-Diels–Alder Reaction
  • Induction
  • Chiral Auxiliaries

Abstract

Abstract The cycloaddition between protonated glyoxylate imines possessing two chiral auxiliaries, N-( S)- or N-( R)-1-phenylethyl and (−)-8-phenylmenthyl or (+)-8-phenylneomenthyl, and cyclopentadiene is described. The absolute configuration of all adducts formed was unequivocally assigned through NMR, specific optical rotation, and X-ray data of appropriated derivatives. Experimental results confirm the highly exo-selectivity for these aza-Diels–Alder reactions, single adducts being obtained from combinations of (8PM)-( R-PEA) and (8PNM)-( S-PEA).

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