An Enantioselective Synthesis of Benzylidene-Protected syn-3,5-Dihydroxy Carboxylate Esters via Osmium, Palladium, and Base Catalysis

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 δ-hydroxy-1-enoates. Th...

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Published inOrganic letters Vol. 3; no. 7; pp. 1049 - 1052
Main Authors Hunter, Thomas J, O'Doherty, George A
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.04.2001
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALDOL ADDITIONS
SELECTIVE ASYMMETRIC DIHYDROXYLATION
METHYL
CONFIGURATION
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Summary: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 δ-hydroxy-1-enoates. The resulting δ-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%).
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol0156188