From pyrrolidin-2-ones to 3-aza-2-oxobicyclo[3.2.0]heptanes. Synthesis of both enantiomers of cis-2-aminomethylcyclobutane carboxylic acid, a conformationally restricted analogue of GABA

Tetrahedron

Volumn 55, Issue 1, 1999, Pages 261-270

  Galeazzi, Roberta ^a   Mobbili, Giovanna ^a   Orena, Mario ^a  

^a UNIVERSITÀ POLITECNICA DELLE MARCHE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOBUTYRIC ACID DERIVATIVE; ACETIC ACID; ALCOHOL; BICYCLO[3.2.0]HEPTANE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CYCLOBUTANE DERIVATIVE; PYRROLIDINE DERIVATIVE; TETRAHYDROFURAN;

ARTICLE; CIS ISOMER; CONFORMATION; CONJUGATE; CYCLIZATION; DIASTEREOISOMER; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0032927046     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01031-X     Document Type: Article

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52. The cyclisation was also performed starting from mesylate 8, but in this case bicyclic compound 9 was isolated in only 53% yield.
53. Following this procedure the previouly observed partial hydrolysis (see ref. 5) of the ester group was suppressed.