紧身衣
化学
对映体药物
非对映体
环丙烷化
立体选择性
组合化学
磷酰胺
硼
对映选择合成
立体化学
有机化学
催化作用
荧光
寡核苷酸
物理
DNA
量子力学
生物化学
作者
Vojtěch Dočekal,Tereza Koberová,Ján Hrabovský,Andrea Vopálenská,Róbert Gyepes,Ivana Cı́sařová,Ramón Rios,Ján Veselý
标识
DOI:10.1002/adsc.202101286
摘要
Abstract The synthesis of enantiopure chiral boron dipyrromethenes (BODIPYs) is of importance due the intrinsic properties of BODIPYs as fluorophores that could be used as probes for molecular sensing. The present study reports an asymmetric organocatalytic cascade reaction of meso ‐chloromethyl BODIPY derivatives with α , β ‐unsaturated aldehydes catalyzed by a chiral secondary amine. The corresponding BODIPY‐derived cyclopropanes were produced in isolated yields 66–98%, and with diastereomeric ratios 3/2–>20/1, and 92–99% ee for major diastereomer. The synthetic utility of the protocol was exemplified on a set of additional transformations of the corresponding optically pure compounds. In addition, a study explaining the reaction mechanism (DFT computations) and photophysical characterization of all enantioenriched products were accomplished. magnified image
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