An efficient, stereoselective approach to syn-1,2-diols protected as cyclic carbonates.
Enantioenriched 4-hydroxyalk-2-ynyl carbonates (or benzoates) have been prepared by stereoselective zinc-mediated addition of alkyl 2-propynyl carbonates (or their benzoate analogues) to aldehydes. Their partial reduction to Z-olefins followed by cyclization under mild Pd-catalyzed conditions allowed a straightforward access to enantioenriched syn-1,2-diols protected as cyclic carbonates.
Georges
Yohan
Y
Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, 08028 Barcelona, Spain. xariza@ub.edu
Allenbach
Yves
Y
Ariza
Xavier
X
Campagne
Jean-Marc
JM
Garcia
Jordi
J