Synthesis 2007(14): 2222-2232  
DOI: 10.1055/s-2007-983759
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© Georg Thieme Verlag Stuttgart · New York

[2+2] Photocycloadditions with Chiral Uracil Derivatives: Access to All Four Stereoisomers of 2-Aminocyclobutanecarboxylic Acid

Carlos Fernandesa, Christine Gauzya, Yi Yanga, Olivier Roya, Elisabeth Pereiraa, Sophie Faurea, David J. Aitken*a,b
a Laboratoire de Synthèse et Etude de Systèmes d’Intérêt Biologique, SEESIB (UMR 6504-CNRS), Département de Chimie, Université Blaise Pascal - Clermont-Ferrand II, 24 Avenue des Landais, 63177 Aubière cedex, France
b Laboratoire de Synthèse Organique et Méthodologie, ICMMO (UMR 8182-CNRS), Université Paris-Sud XI, Bât. 420, 15 rue Georges Clemenceau, 91405 Orsay cedex, France
Fax: +33(1)69156278; e-Mail: David.Aitken@icmo.u-psud.fr;
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Publikationsverlauf

Received 28 February 2007
Publikationsdatum:
03. Juli 2007 (online)

Abstract

Starting from a single, chiral, bicyclic derivative of uracil, all four stereoisomers of 2-aminocyclobutanecarboxylic acid have been prepared in enantiomerically pure form, using a synthetic sequence which begins with a key photochemical [2+2] cycloaddition reaction and includes a practical cis to trans β-amino acid isomerisation procedure.

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Crystallographic data for (-)-13a: C14H14N2O2, M = 242.27, T = 293 K, space group P61, a = 8.3788 (4) Å, b = 8.3788 (4) Å, c = 28.4565 (17) Å, α = 90.00°, β = 90.00°, γ = 120.00°, Z = 6, V = 1730.12 (16) Å3, ρcalcd = 1.395 g/cm-3. Full crystallographic data have been deposited with the Cambridge Crystallographic Data Centre (CCDC) as supplementary publication number CCDC 626949. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK, fax: +44(1223)336033, e-mail: deposit@ccdc.cam.ac.uk.