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Synthesis of 3‐Azabicyclo[3.2.0]heptane Derivatives as γ‐Aminobutyric Acid Analogues through Intermolecular [2+2] Photocycloaddition
Author(s) -
Petz Susanne,
Wanner Klaus T.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201723
Subject(s) - chemistry , cycloaddition , bicyclic molecule , intermolecular force , heptane , maleic anhydride , acid anhydride , maleic acid , organic chemistry , stereochemistry , molecule , polymer , catalysis , epoxy , copolymer
The synthesis of 3‐azabicyclo[3.2.0]heptane‐6‐carboxylic acid and 7‐substituted derivatives was developed as bicyclic analogues of γ‐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.