Tetrahedron Letters p. 6301 - 6304 (1985)
Update date:2022-08-04
Topics:
McCombie, Stuart W.
Shankar, Bandarpalle B.
Ganguly, Ashit K.
E-2-(Phenylsulfonyl)vinyl ethers of 2,3-epoxyalcohols are stereospecifically rearranged to 3-(phenylsulfonyl)-4-(1-hydroxyalkyl)-4,5-dihydrofurans on treatment with LDA.Oxidation of these compounds or the derived des-sulfonyl compounds provides esters or lactones which correspond to regiospecific delivery of -CO2H or -CH2CO2H to C-2, with inversion.
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