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

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

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...

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Veröffentlicht in:Synthesis (Stuttgart) 2007-07, Vol.2007 (14), p.2222-2232
Hauptverfasser: Fernandes, Carlos, Gauzy, Christine, Yang, Yi, Roy, Olivier, Pereira, Elisabeth, Faure, Sophie, Aitken, David J.
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Sprache:eng
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Zusammenfassung: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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2007-983759