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Application du rearrangement de Claisen aux -1 alcen-1(Z) ols-3. Syntheses d'alcadien-2(E),4(E) oates d'ethyle et de (p.toluenesulfonylamino)-5 alcen-3(E) ols-1
Lorne, Robert,Julia, Sylvestre A.
, p. 317 - 324 (2007/10/02)
The acid catalysed reaction between 1--1(Z)-alken-3-ols 1 and ethyl orthoacetate takes place via a Claisen rearrangement to give stereoselectively the ethyl-3-(1',1'-dimethylethyl)thio-4(E)-alkenoates 2a, b, c.Oxone oxidation converts these sulfide-esters 2 into the corresponding sulfone-esters 6a, b, c, which on treatment with sodium carbonate give the ethyl 2(E),4(E) alkadienoates 7a, b, c.Treatment of the sulfide-esters 2 with chloramine T yields compounds 10a, b, c through a sigmatropic rearrangement of the intermediate N-tosyl-sulfimines.These compounds 10 are reduced by DIBAL-H to the 5-(p.toluenesulfonylamino)-3(E) alken-1-ols 11a, b, c.
