Faculty of Pharmaceutical Sciences, Hokkaido University , Sapporo 060-0812, Japan.
Org Lett. 2014 Jan 3;16(1):14-7. doi: 10.1021/ol403099f. Epub 2013 Dec 6.
In the presence of CsF, a wide range of α-substituted α-siloxy silanes were carboxylated under a CO2 atmosphere (1 atm) via Brook rearrangement. A variety of α-substituents including aryl, alkenyl, and alkyl groups were tolerated to afford α-hydroxy acids in moderate-to-high yields. One-pot synthesis from aldehydes using PhMe2SiLi and CO2 was also possible, providing α-hydroxy acids without the isolation of an α-hydroxy silane.
在 CsF 的存在下，通过 Brook 重排，在 CO2 气氛（1 大气压）下，α-取代的α-硅氧基硅烷可实现广泛的羧化反应。各种 α-取代基，包括芳基、烯基和烷基，都可耐受，以中等至高产率得到α-羟基酸。使用 PhMe2SiLi 和 CO2 从醛一锅合成也是可能的，无需分离α-羟基硅烷即可提供α-羟基酸。
