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Practical Syntheses of Both Enantiomers of the Conformationally Restricted GABA Analogue cis ‐(2‐Aminocyclobutyl)acetic Acid
Author(s) -
Awada Hawraà,
Robin Sylvie,
Guillot Régis,
Yazbeck Ogaritte,
Naoufal Daoud,
Jaber Nada,
Hachem Ali,
Aitken David J.
Publication year - 2014
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.201402676
Subject(s) - chemistry , enantiomer , intramolecular force , derivatization , acetic acid , stereochemistry , derivative (finance) , absolute configuration , chiral auxiliary , combinatorial chemistry , enantioselective synthesis , organic chemistry , high performance liquid chromatography , catalysis , financial economics , economics
Two efficient routes have been established for the preparation of both enantiomers of cis ‐(2‐aminocyclobutyl)acetic acid, a conformationally restricted analogue of GABA. Both procedures converged on the racemic N ‐ tert ‐butoxycarbonyl derivative of the target compound, which was resolved through chiral derivatization with an oxazolidinone auxiliary, which also allowed determination of the absolute configuration of the new compounds. The first route involved the homologation of cis ‐2‐aminocyclobutanecarboxylic acid, whereas the second route employed an intramolecular photocyclization protocol, which provided an expedient, cis ‐selective access to the lactam form of the target structure.