Journal
ORGANIC LETTERS
Volume 7, Issue 26, Pages 5913-5915Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol052544h
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[GRAPHICS] The enantioselective [2,3]-Wittig rearrangement of 1-allyloxy-1-(naphthalen-2-yl)-4-siloxy-2,4-pentadienyl anion, derived from optically enriched 4,5-epoxy-1-(naphthalen-2-yl)-5-silyl-2-pentenyl allyl ether via a base-induced ring opening of the epoxide followed by Brook rearrangement, has been studied. The chirality of the epoxide was transferred to the alcohols in up to 97% ee, depending on the solvent used. The best result was obtained in 1,4-dioxane at a temperature above room temperature.
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