Stereoselective synthesis of nipecotic acid derivatives via palladium-catalyzed decarboxylative cyclization of γ-methylidene-δ- valerolactones with imines

Organic Letters

Volumn 11, Issue 2, 2009, Pages 457-459

  Shintani, Ryo ^a   Murakami, Masataka ^a   Hayashi, Tamio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DELTA VALEROLACTONE; DELTA-VALEROLACTONE; IMINE; NIPECOTIC ACID; NIPECOTIC ACID DERIVATIVE; PALLADIUM; PHOSPHINE; PHOSPHINE DERIVATIVE; PYRONE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; DECARBOXYLATION; ENZYME SPECIFICITY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; CYCLIZATION; DECARBOXYLATION; IMINES; NIPECOTIC ACIDS; PALLADIUM; PHOSPHINES; PYRONES; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 61449092838     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802569q     Document Type: Article

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20. 5) (2.1 mg, μmol) and dppf (6.1 mg, 11 μmol) in toluene (0.50 mL) was stirred for 10 min at room temperature. Lactone l (0.20 mmol) and imine 2 (0.24 mmol) were added to it with additional toluene (0.50 mL), and the resulting solution was stirred for 24 h at 20 °C. The reaction mixture was directly passed through a pad of silica gel with EtOAc, and the solvent was removed under vacuum. The residue was purified by silica gel preparative TLC to afford compound 3.
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