An Enantioselective Synthesis of Benzylidene-Protectedsyn-3,5-Dihydroxy Carboxylate Esters via Osmium, Palladium, and Base Catalysis
- 6 March 2001
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 3 (7) , 1049-1052
- https://doi.org/10.1021/ol0156188
Abstract
[reaction: see text]. The enantioselective syntheses of several protected syn-3,5-dihydroxy carboxylic esters have been achieved from the corresponding achiral 1,3-dieneoates. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form delta-hydroxy-1-enoates. The resulting delta-hydroxy-1-enoates are subsequently converted into benzylidene-protected 3,5-dihydroxy carboxylic esters in one step. The benzylidene-protected 3,5-dihydroxy carboxylic esters are produced in good overall yields (25% to 51%) and high enantiomeric excesses (80% to >95%).Keywords
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