A novel conversion of erythro phospholane epoxides to one-carbon atom homologated allylic alcohols

Tetrahedron Letters

Volumn 45, Issue 13, 2004, Pages 2851-2854

  Reddy, Valluru Krishna ^a   Haritha, Buchammagari ^a   Oshikawa, Tatsuo ^b   Yamashita, Mitsuji ^a  

^a SHIZUOKA UNIVERSITY   (Japan)

^b NUMAZU COLLEGE OF TECHNOLOGY   (Japan)

Author keywords

Dimethylsulfonium methylide; Epoxide homologation; Hetero sugars; Phospha sugars

Indexed keywords

ALLYL ALCOHOL; CARBON; EPOXIDE; OXIDE; PHOSPHORUS DERIVATIVE; SULFONIUM DERIVATIVE;

ARTICLE; ATOM; METHODOLOGY; STRUCTURAL HOMOLOGY; SYNTHESIS;

EID: 1542268867     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.01.139     Document Type: Article

References (22)

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18. -1) 2960 (C-H of epoxide), 1270 and 828 (epoxide), 1194 (P=O).
19. Preparation of allylic alcohols (5a-g ). Representative compound 5a:To a -20°C suspension of trimethylsulfonium iodide (1.2 g, 6.0 mmol, 6.1 equiv) in THF (10 mL) was added n-BuLi (4.0 mL of 1.6 M hexane solution, 6.4 mmol, 6.5 equiv). After 30-40 min, epoxide 4a (0.2 g, 0.97 mmol, 1.0 equiv) in THF (5 mL) was introduced and the reaction slowly allowed to warm to 0°C over 1 h; the reaction mixture was then stirred at ambient temperature for 2 h. The reaction was quenched with water and extracted with chloroform. The combined extracts were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residues were purified on silica gel flash column chromatography (20:1 chloroform-methanol) and recycle GPC analysis to give pure allylic alcohol 5a as oily liquid.
20. To prepare sulfide derivatives, see: Krishna Reddy V., Onogawa J.I., Rao L.N., Oshikawa T., Takahashi M., Yamashita M. J. Heterocycl. Chem. 39:2002;69-75.
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