A Sakurai-Prins-Ritter reaction sequence for the diastereoselective synthesis of 4-amidotetrahydropyrans catalyzed by bismuth triflate

Tetrahedron Letters

Volumn 49, Issue 40, 2008, Pages 5727-5731

  Sabitha, Gowravaram ^a   Bhikshapathi, M ^a   Nayak, Sambit ^a   Yadav, J S ^a   Ravi, R ^a   Kunwar, A C ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Aldehydes; Allyltrimethylsilane; Bi(OTf)3 4H2O; Diastereoselectivity; Sakurai Prins Ritter; Tetrahydropyrans

Indexed keywords

BISMUTH DERIVATIVE; N1 (2,6 DIETHYLTETRAHYDRO 2H 4 PYRANYL)BENZAMIDE; N1 (2,6 DIHEPTYLTETRAHYDRO 2H 4 PYRANYL)BENZAMIDE; N1 (2,6 DIISOPROPYLTETRAHYDRO 2H 4 PYRANYL)ACETAMIDE; N1 (2,6 DIPENTYLTETRAHYDRO 2H 4 PYRANYL)ACETAMIDE; N1 (2,6 DIPHENYLTETRAHYDRO 2H 4 PYRANYL)BENZAMIDE; N1 (2,6 DIPROPYLTETRAHYDRO 2H 4 PYRANYL)ACETAMIDE; N1 (2,6 DIPROPYLTETRAHYDRO 2H 4 PYRANYL)BENZAMIDE; N1 [2,6 DI(2,6 DIMETHOXYPHENYL)TETRAHYDRO 2H 4 PYRANYL]BENZAMIDE; N1 [2,6 DI(4 FLUOROPHENYL)TETRAHYDRO 2H 4 PYRANYL]BENZAMIDE; N1 [2,6 DI(4 METHYLPHENYL)TETRAHYDRO 2H 4 PYRANYL]BENZAMIDE; TETRAHYDROPYRAN DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CATALYSIS; CATALYST; STEREOCHEMISTRY; SYNTHESIS;

EID: 49649119624     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.07.079     Document Type: Article

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51. 2O (10 mol %) in nitrile (5 mL), and the reaction mixture was stirred at room temperature for the specified time. After completion of the reaction (as indicated by TLC), the reaction mixture was quenched with water and extracted with ethyl acetate (2 × 5 mL)
52. 4), and concentrated to leave a crude compound which was subjected to flash column chromatography using 4:1 hexane, ethyl acetate solvent as eluent to afford a pure compound
53. 4), and concentrated to leave a crude compound which was subjected to flash column chromatography using 4:1 hexane
54. 4), and concentrated to leave a crude compound which was subjected to flash column chromatography using 4:1 hexane, ethyl acetate solvent as eluent to afford a pure compound