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1 article(s) from Braunschweig, Holger

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

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Graphical Abstract

Figure 1: The conformationally rigid amino acid derivatives 1–3 (β-turn-inducing building blocks) and 4–6 (su...

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Figure 2: The targeted tricyclic amino acid derivatives 7 and 8, and the key intermediate 9.

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Scheme 1: Synthesis of the racemic ketone rac-9. i) NH₄OAc, HOAc, Δ, 4 d, 100%; ii) LiAlH₄, THF, Δ, 1 d, 87% [24]...

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Scheme 2: Enantioselective hydrosilylation/oxidation of 11. i) HSiCl₃, [Pd(C₃H₅)Cl]₂ (0.06 mol %), (R)-MOP (0...

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Figure 3: X-ray crystal structure of 9. X-ray data have been deposited with the Cambridge Crystallographic Da...

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Scheme 3: Initial route to the aldehyde rac-15. i) MePPh₃⁺Br⁻, t-BuOK, toluene, Δ, 7 h, 77% or Mg, TiCl₄, CH₂...

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Scheme 4: Assembly of the amino acid 7a•HCl and the N-tosylamide 7b•HCl. i) MeOCH₂PPh₃⁺Cl⁻, t-BuOK, toluene/T...

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Scheme 5: Preparation of the amino acid 8a•HCl and the N-tosylamide 8b•HCl. i) TMSCH₂CO₂Et, LDA, THF, −78 °C ...

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Figure 4: X-ray crystal structure of 8a•MeOH. X-ray data have been deposited with the Cambridge Crystallograp...

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Published 21 Dec 2009

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

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