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Updated: Jul 19, 2026

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
1-phenylprop-2-ynyl acetate: a useful building block for the stereoselective construction of polyhydroxylated chains
Xavier Ariza1, Jordi Garcia, Yohan Georges
1Departament de Química Orgànica, Universitat de Barcelona, Martí i Franquès 1, 08028 Barcelona, Spain. xariza@ub.edu
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.
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