Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 71, Issue 20, Pages 7741-7746Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo061200h
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Funding
- NIGMS NIH HHS [R01 GM063150, GM63150, R01 GM063150-01A1] Funding Source: Medline
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The enantioselective syntheses of several protected 4-substituted syn-3,5-dihydroxy carboxylic esters have been achieved from the corresponding achiral (E,E)- or (E,Z)-1,3-dienoates. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form gamma-substituted delta-hydroxy-1-enoates. The resulting delta-hydroxy-1-enoates are subsequently converted into benzylidene-protected 4-substituted syn-3,5-dihydroxy carboxylic esters in one step. The benzylidene-protected 3,5-dihydroxy carboxylic esters are produced in good overall yields (20-54%) and high enantiomeric excess (73- 97% ee).
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