期刊
ORGANIC LETTERS
卷 19, 期 9, 页码 2282-2285出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b00811
关键词
-
资金
- National Natural Science Foundation of China [21602073, 21572078]
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.
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