Beilstein Journal of Organic Chemistry (Dec 2009)

Enantioselective synthesis of tricyclic amino acid derivatives based on a rigid 4-azatricyclo[5.2.1.02,6]decane skeleton

  • Matthias Breuning,
  • Tobias Häuser,
  • Christian Mehler,
  • Christian Däschlein,
  • Carsten Strohmann,
  • Andreas Oechsner,
  • Holger Braunschweig

DOI
https://doi.org/10.3762/bjoc.5.81
Journal volume & issue
Vol. 5, no. 1
p. 81

Abstract

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An enantioselective route to four tricyclic amino acids and N-tosylamides, composed of a central norbornane framework with a 2-endo,3-endo-annelated pyrrolidine ring and a 5-endo-C1 or -C2 side chain, has been developed. A key intermediate was the chiral, N-Boc-protected ketone (1R,2S,6S,7R)-4-azatricyclo[5.2.1.02,6]decan-8-one, available from inexpensive endo-carbic anhydride in five steps and 47% yield. The rigid scaffold makes these amino acid derivatives promising candidates for β-turn-inducing building blocks in peptidomimetics and for chiral auxiliaries in asymmetric organocatalysis.

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