Directed methallylations as a synthetic route to 1,3-polyols

Tetrahedron Letters

Volumn 39, Issue 15, 1998, Pages 2039-2042

  Brzezinski, Linda Joy ^a   Leahy, James W ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 POLYOL DERIVATIVE; HENNOXAZOLE F; POLYOL; TETRACYCLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; METHYLATION; ORGANIC CHEMISTRY; OUTCOMES RESEARCH; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0032499081     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00182-8     Document Type: Article

References (21)

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17. 13C (75 MHz) NMR spectra. Diastereomeric ratios were determined via analysis of the NMR spectra of the mixtures after chromatographic purification.
18. 3 (8.5 g, 82 mmol) in THF (20 mL) was added such that the reaction temperature remained below -60 °C and the reaction was then stirred at -78 °C for 4 h prior to warming to 0 °C. An aqueous solution of 3 N HCl saturated with NaCl (50 mL) was added and the mixture was stirred vigorously until the upper organic layer remained clear. The layers were separated and the organic layer was used directly in the methallylation studies without purification. The solution could be titrated by reaction with benzaldehyde, and was typically found to to be approximately 0.15 M.
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20. 14
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