Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 19, Pages 4017-4025Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201201723
Keywords
Nitrogen heterocycles; Neurotransmitters; Amino acids; Photochemistry; Cycloaddition
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The synthesis of 3-azabicyclo[3.2.0]heptane-6-carboxylic acid and 7-substituted derivatives was developed as bicyclic analogues of -aminobutyric acid. A sensitized, intermolecular [2+2] photocycloaddition of maleic anhydride with N-protected 3-pyrroline served as the key step in these syntheses. Upon transformation of the anhydride function of the primary cycloaddition product, 6-monosubstituted and 6,7-disubstituted 3-azabicyclo[3.2.0]heptane derivatives were obtained.
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