Stereoselective cyclization using palladium(II) catalyst via hemiacetal intermediates

Tetrahedron Letters

Volumn 45, Issue 14, 2004, Pages 2883-2886

  Miyazawa, Masahiro ^a   Hirose, Yukari ^a   Narantsetseg, Magsarjav ^a   Yokoyama, Hajime ^a   Yamaguchi, Seiji ^a   Hirai, Yoshiro ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

Cyclization; Hemiacetal; Palladium catalyst; Tetrahydropyran

Indexed keywords

3 PHENYL 7 HYDROXY 5 HEPTENAL; ACETAL DERIVATIVE; BENZENE DERIVATIVE; HEMIACETAL; PALLADIUM; TETRAHYDROPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; CYCLIZATION; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 1642328126     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.02.058     Document Type: Article

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20. 2 (4 mg, 0.01 mmol) in THF (4.4 mL) was added abs ethanol (0.03 mL, 0.47 mmol) and a solution of aldehyde 15 (62 mg, 0.21 mmol) in THF (2 mL) at room temperature under an argon atmosphere. The mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with diethyl ether, and the solution was filtered through a Florisil pad. The pad was washed with diethyl ether. The combined organic layer was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel ( eluent with hexane/ethyl acetate=97:3 ) to afford 35 mg (70%) of 17a as a colorless oil.