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Issue 41, 2014
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Stereoselective intermolecular [2 + 2]-photocycloaddition reactions of maleic anhydride: stereocontrolled and regiocontrolled access to 1,2,3-trifunctionalized cyclobutanes

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Abstract

Short synthetic sequences commencing with the photosensitized [2 + 2]-cycloaddition reactions of maleic anhydride with either allyl alcohol or propargyl alcohol have been elaborated to provide access to 1,2,3-trisubstituted cyclobutanes with three differentiated one-carbon substituents and complementary stereochemical patterns. These intermediates were used to prepare three discrete stereo- and regioisomers of hydroxymethylated cyclobutane β-amino acids in orthogonally protected form.

Graphical abstract: Stereoselective intermolecular [2 + 2]-photocycloaddition reactions of maleic anhydride: stereocontrolled and regiocontrolled access to 1,2,3-trifunctionalized cyclobutanes

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Publication details

The article was received on 02 Jul 2014, accepted on 20 Aug 2014 and first published on 20 Aug 2014


Article type: Paper
DOI: 10.1039/C4OB01383B
Org. Biomol. Chem., 2014,12, 8212-8222

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    Stereoselective intermolecular [2 + 2]-photocycloaddition reactions of maleic anhydride: stereocontrolled and regiocontrolled access to 1,2,3-trifunctionalized cyclobutanes

    F. Hernvann, G. Rasore, V. Declerck and D. J. Aitken, Org. Biomol. Chem., 2014, 12, 8212
    DOI: 10.1039/C4OB01383B

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