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 (free Supporting Information)
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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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