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Please login to access the full content or check if you have access via9.9.4.5.3 Method 3: Wittig Rearrangement of Alkyl 3-Furylmethyl Ether
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König, B., Science of Synthesis, (2001) 9, 270.
The Wittig rearrangement of an alkyl 3-furylmethyl ether 429 gives 3-substituted 430 and 2,3-disubstituted furans 431, derived from [1,2]- or [2,3]-sigmatropic shifts whose ratios depend on the reaction conditions and R1 (Scheme 134).[721] When R1 is a vinyl group and the base used is tert-butyllithium, the ratio of [1,2]-rearrangement products and [2,3]-rearrangement products is >95:<5. When R1 is a carboxy group and the base is lithium diisopropylamide, only [2,3]-rearrangement product 431 is observed. The reaction sequence has been used for the synthesis of dendrolasin (433) from 3-(hydroxymethyl)furan (432) and geranyl bromide (Scheme 134).
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References
[721] | Meeeeee, M.; Meeee, M.; Meeee, M., M. Meee. Mee., Meee. Meeeee., (8888), 8888. |