Synthesis of tetrahydrofurans by the reaction of α,β-epoxy alcohol derivatives with allylsilanes

Tetrahedron Letters

Volumn 40, Issue 32, 1999, Pages 5877-5880

  Sugita, Yoshiaki ^a   Kimura, Yoko ^a   Yokoe, Ichiro ^a  

^a JOSAI UNIVERSITY   (Japan)

Author keywords

Cycloadditions; Epoxides; Sakurai Hosomi reaction

Indexed keywords

ALCOHOL DERIVATIVE; EPOXIDE; SILANE DERIVATIVE; TETRAHYDROFURAN DERIVATIVE; TIN CHLORIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0033529868     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01089-8     Document Type: Article

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21. 4. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-AcOEt = 60:1) to give the cycloadduct (6a), homoallylalcohol (10), and chlorohydrin (14) in 76%, 4%, and 4% yields, respectively.
22. 4 gave the cycloadduct (6a) in low yield (4%) and 1 was recovered in 46% yield.
23. 2 (1.2 ml) over 1 h period at -50 °C under an argon atmosphere. After workup was performed as detailed in procedure A, the cycloadduct (24a) was obtained in 79% yield.
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