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

被引：45

作者：

Mita, Tsuyoshi ^{[1
]}

Higuchi, Yuki ^{[1
]}

Sato, Yoshihiro ^{[1
,2
]}

机构：

[1] Hokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan

[2] Japan Sci & Technol Agcy JST, ACT C, Sapporo, Hokkaido 0600812, Japan

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 01期

关键词：

METAL-CATALYZED CARBOXYLATION; CARBON-DIOXIDE; NUCLEATION INHIBITION; AMINO-ACIDS; REAGENTS; ALKENES; SALTS; TRANSFORMATION; RESOLUTION; ALKYNES;

D O I：

10.1021/ol403099f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the presence of CsF, a wide range of alpha-substituted alpha-siloxy silanes were carboxylated under a CO2 atmosphere (1 atm) via Brook rearrangement. A variety of alpha-substituents including aryl, alkenyl, and alkyl groups were tolerated to afford alpha-hydroxy acids in moderate-to-high yields. One-pot synthesis from aldehydes using PhMe2SiLi and CO2 was also possible, providing alpha-hydroxy acids without the isolation of an alpha-hydroxy silane.

引用

页码：14 / 17

页数：4

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