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- Title
Divergent and Stereoselective Synthesis of β-Silyl-α-Amino Acids through Palladium-Catalyzed Intermolecular Silylation of Unactivated Primary and Secondary C−H Bonds.
- Authors
Liu, Yue-Jin; Liu, Yan-Hua; Zhang, Zhuo-Zhuo; Yan, Sheng-Yi; Chen, Kai; Shi, Bing-Feng
- Abstract
A general and practical PdII-catalyzed intermolecular silylation of primary and secondary C−H bonds of α-amino acids and simple aliphatic acids is reported. This method provides divergent and stereoselective access to a variety of optical pure β-silyl-α-amino acids, which are useful for genetic technologies and proteomics. It can also be readily performed on a gram scale and the auxiliary can be easily removed with retention of configuration. The synthetic importance of this method is further demonstrated by the late-stage functionalization of biological small molecules, such as (−)-santonin and β-cholic acid. Moreover, several key palladacycles were successfully isolated and characterized to elucidate the mechanism of this β−C(sp3)-H silylation process.
- Subjects
STEREOSELECTIVE reactions; CHEMICAL synthesis; AMINO acids; PALLADIUM catalysts; SILYLATION; CARBON-hydrogen bonds
- Publication
Angewandte Chemie International Edition, 2016, Vol 55, Issue 44, p13859
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201607766