title: 1-phenylprop-2-ynyl acetate: a useful building block for the stereoselective construction of polyhydroxylated chains.
abstract: (R)- or (S)-1-phenylprop-2-ynyl acetate was added stereoselectively to aldehydes to afford 4-hydroxy-1-phenylalk-2-ynyl acetates. The transformation of such adducts into the corresponding allylic 1,4-diacetates allowed a highly efficient transfer of chirality from C1 to C3 by a regio- and stereoselective [3,3]-sigmatropic rearrangement. The obtained unsaturated 1,2-diacetates were useful synthetic intermediates whose double bond and/or phenyl group were transformed in different aldehydes, acids, or esters.
authors.affiliation: Departament de Química Orgànica, Universitat de Barcelona, Martí i Franquès 1, 08028 Barcelona, Spain. xariza@ub.edu
authors.forename: Xavier
authors.initials: X
authors.lastname: Ariza
authors.forename: Jordi
authors.initials: J
authors.lastname: Garcia
authors.forename: Yohan
authors.initials: Y
authors.lastname: Georges
authors.forename: Mar
authors.initials: M
authors.lastname: Vicente