Liu, Yue-Jin and Liu, Yan-Hua and Zhang, Zhuo-Zhuo and Yan, Sheng-Yi and Chen, Kai and Shi, Bing-Feng (2016) Divergent and Stereoselective Synthesis of β-Silyl-α-Amino Acids through Palladium-Catalyzed Intermolecular Silylation of Unactivated Primary and Secondary C−H Bonds. Angewandte Chemie, 55 (44). pp. 13859-13862. ISSN 0044-8249. https://resolver.caltech.edu/CaltechAUTHORS:20161004-083417715
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Abstract
A general and practical Pd^(II)-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(sp^3)-H silylation process.
Item Type: | Article | |||||||||
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Additional Information: | © 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Received: August 11, 2016. Revised: September 10, 2016. Published online: September 28, 2016. Financial support from the National Basic Research Program of China (2015CB856600) and the NSFC (21572201, 21422206) is gratefully acknowledged. | |||||||||
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Subject Keywords: | amino acids; asymmetric transformations; chiral auxiliaries; C-H activation; silylation | |||||||||
Issue or Number: | 44 | |||||||||
Record Number: | CaltechAUTHORS:20161004-083417715 | |||||||||
Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20161004-083417715 | |||||||||
Official Citation: | Y.-J. Liu, Y.-H. Liu, Z.-Z. Zhang, S.-Y. Yan, K. Chen, B.-F. Shi, Angew. Chem. Int. Ed. 2016, 55, 13859. | |||||||||
Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
ID Code: | 70789 | |||||||||
Collection: | CaltechAUTHORS | |||||||||
Deposited By: | Tony Diaz | |||||||||
Deposited On: | 04 Oct 2016 18:45 | |||||||||
Last Modified: | 17 Dec 2019 00:12 |
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