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An Efficient, Stereoselective Approach to syn-1,2-Diols Protected as Cyclic Carbonates
journal contribution
posted on 2004-10-15, 00:00 authored by Yohan Georges, Yves Allenbach, Xavier Ariza, Jean-Marc Campagne, Jordi GarciaEnantioenriched 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.