Enantioselective synthesis of tricyclic amino acid derivatives based on a rigid 4-azatricyclo[5.2.1.0^2,6]decane skeleton

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

Beilstein J. Org. Chem. 2009, 5, No. 81, doi:10.3762/bjoc.5.81

• peptide building blocks and as bifunctional organocatalysts. In this paper we report on the first enantioselective synthesis of 7 and 8, which was achieved via the chiral ketone 9 as the key intermediate. Results and Discussion The key intermediate, the tricyclic amino ketone 9, was first prepared in

• are promising candidates as ß-turn-inducing building blocks in peptidomimetics and as chiral auxiliaries in organocatalysis. The conformationally rigid amino acid derivatives 1–3 (β-turn-inducing building blocks) and 4–6 (successful organocatalysts). The targeted tricyclic amino acid derivatives 7 and