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An efficient, stereoselective approach to syn-1,2-diols protected as cyclic carbonates
Yohan Georges1, Yves Allenbach, Xavier Ariza
1Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, 08028 Barcelona, Spain. xariza@ub.edu
The Journal of Organic Chemistry
|October 9, 2004
Abstract:
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.