期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 75, 期 20, 页码 6842-6847出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo1011653
关键词
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An enantioselective method for the synthesis alpha-methyl carboxylic acids starting from trans-cinnamaldehyde, a readily available and inexpensive compound. has been developed Allylic alcohol I was obtained via a stand:lid Grignard addition to tras-cinnainaldehyde Dynamic kinetic resolution was applied to allylic alcohol I utilizing a ruthenium catalyst and either an (R)-selective lipase 01 selective protease to provide the corresponding allylic esters in high yield and high cc A copper catalyzed allylic substitution was then applied to provide the corresponding alkenes with inversion of stereochemistry Subsequent C C double bond cleavage afforded pharmaceutically important alpha-methyl substituted carboxylic. acid in high cc and over all yields of up to 76%.
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