Regioselective and stereoselective reductive cleavage of 1,7-dioxaspiro[5.5]undecane alcohols

Tetrahedron Letters

Volumn 37, Issue 32, 1996, Pages 5649-5652

  Crimmins, Michael T ^a   Rafferty, Stephen W ^a  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

Author keywords

1,7 dixaspiro 5.5 undecanes; reductive cleavage; spiroketals; tetrahydropyrans

Indexed keywords

TETRAHYDROPYRAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030570850     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01196-3     Document Type: Article

References (24)

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18. 13C, and IR spectra as well as satisfactory C, H combustion analyses or HRMS. All yields are for homogeneous, chromatographically pure products unless otherwise indicated.
19. 3SiH. The mixture was stirred for 10 min whereupon a solution of the Lewis acid (1.0 equiv) was added dropwise. After stirring at -78°C for 4 h (for trialkylsilyl or benzyl derivatives), or warming to 25°C for 4 - 6 h (for the alcohols), the reaction was quenched with aqueous sodium bicarbonate and diluted with water. The aqueous layer was extracted with dichloromethane and the combined organic layers were combined, dried and concentrated. After determination of isomeric ratio of the crude product by NMR, the residue was purified by silica gel chromatography.
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24. 14. The major product from this reaction was the enol ether below. (formula presented)