4-isopropenyl-3-tosylmethyl pyrrolidines through radical cyclizations of 4-aza-1,6-dienes - An approach to kainic acids -

Tetrahedron Letters

Volumn 37, Issue 8, 1996, Pages 1229-1232

  Bertrand, M P ^a   Gastaldi, S ^a   Nouguier, R ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

KAINIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030022369     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00006-8     Document Type: Article

References (33)

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33. In a typical experiment, a mixture containing 4 (15 mg, 0.048 mmol) and AIBN (2 mg, 0.012 mmol) was added by portions, under inert atmosphere, to a previously degassed refluxing solution of 10 (140 mg, 0.32 mmol) in benzene (25 ml). After 6 h, the solvant was evaporated and the residue was purified by flash chromatography on silicagel (EtOAc/pentane; 25/75). The isolated mixture contained 7a and 7 b in a 54 : 46 ratio (130 mg, 0.30 mmol, 94%). Pure samples of each isomer were further isolated from semi-preparative HPLC (EtOAc/2,2,3-Trimethylpentane; 20/80).