Tetrahedron letters

[2, 3]-Wittig rearrangement by a chlorine–lithium exchange

B Maciá, C Gómez, M Yus

文献索引：Macia, Beatriz; Gomez, Cecilia; Yus, Miguel Tetrahedron Letters, 2005 , vol. 46, # 36 p. 6101 - 6104

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被引用次数: 6

摘要

The reaction of different allylic chloromethyl ethers with an excess of lithium powder (1: 7 molar ratio) and a catalytic amount of DTBB (2.5 mol%) in THF at 0° C for 1h gives, after hydrolysis with water, the expected alcohols resulting from a [2, 3]-Wittig rearrangement, in an exclusive manner. The same process can also be applied to the corresponding [1, 2]- Wittig rearrangement, as it is exemplified for benzyl chloromethyl ether.