Carboxylation with CO₂ via Brook Rearrangement: Preparation of α-Hydroxy Acid Derivatives

Tsuyoshi Mita*, Yuki Higuchi and Yoshihiro Sato*

*Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan, Email: tmitapharm.hokudai.ac.jp, biyopharm.hokudai.ac.jp

T. Mita, Y. Higuchi, Y. Sato, Org. Lett., 2014, 16, 14-17.

DOI: 10.1021/ol403099f

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Abstract

In the presence of CsF, a wide range of α-substituted α-siloxy silanes were carboxylated under 1 atm of CO₂ via Brook rearrangement. Various α-substituents including aryl, alkenyl, and alkyl groups were tolerated to afford α-hydroxy acids in good yields. A one-pot synthesis from aldehydes using PhMe₂SiLi and CO₂ provides α-hydroxy acids without the need for isolation of the α-hydroxy silane.

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Key Words

α-hydroxy carboxylic acids, Brook Rearrangement

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ID: J54-Y2014