Organocatalyzed Direct Aldol Reaction of Silyl Glyoxylates for the Synthesis of α-Hydroxysilanes
Organocatalyzed Direct Aldol Reaction of Silyl Glyoxylates for the Synthesis of α-Hydroxysilanes
复制标题
有机催化乙醛酸甲硅烷基酯直接羟醛反应合成 α-羟基硅烷
DOI：
10.1021/acs.orglett.7b00811
复制
发表时间：
2017-05-05
期刊：
影响因子：
5.2
通讯作者：
Wang, Lei
中科院分区：
文献类型：
--
作者：
Han, Man-Yi;Xie, Xiaoyu;Wang, Lei
A novel organocatalyzed direct aldol reaction of aldehydes to silyl glyoxylates is disclosed. This method provides an efficient route to alpha-hydroxysilanes with excellent enantioselectivities (up to 99% ee) and high diastereoselectivities (up to >20:1 dr). In the new activation model of silyl glyoxylates, the hydrogen bond is critical to the reaction. A carbonyl group directly attached to silicon in acylsilanes could be activated by coordination to the proton of hydroxyl and carboxylic acid via a hydrogen bond. Moreover, commercially available cis-L-4-hydroxyproline is an ideal organocatalyst for activating both aldehydes and acylsilanes.
