Efficient synthesis of 3-hydroxymethylated cis- and trans- cyclobutane b-amino acids using an intramolecular photocycloaddition strategy

Efficient synthesis of 3-hydroxymethylated cis- and trans- cyclobutane b-amino acids using an intramolecular photocycloaddition strategy

Uracil bearing a tethered allyl alcohol appendage at N1 undergoes a [2+2] photocycloaddition reaction to provide a single tricyclic adduct in high yield. This compound is transformed in one step into a cis-cyclobutane β-amino acid bearing a 3-hydroxymethyl group. Through appropriate functionalizatio...

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Veröffentlicht in:Tetrahedron 2008, Vol.64, p.1088-1093
Hauptverfasser: Mondiere, Aurélie, Peng, Runhui, Remuson, Roland, Aitken, D.J.
Format: Artikel
Sprache:eng
Schlagworte:
Chemical Sciences
Organic chemistry
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Zusammenfassung:Uracil bearing a tethered allyl alcohol appendage at N1 undergoes a [2+2] photocycloaddition reaction to provide a single tricyclic adduct in high yield. This compound is transformed in one step into a cis-cyclobutane β-amino acid bearing a 3-hydroxymethyl group. Through appropriate functionalization and epimerization, the trans isomer is obtained therefrom in only three further steps.
ISSN:0040-4020
DOI:10.1016/j.tet.2007.11.021