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Divergent and Stereoselective Synthesis of β-Silyl-α-Amino Acids through Palladium-Catalyzed Intermolecular Silylation of Unactivated Primary and Secondary C−H Bonds

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. http://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
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/ange.201607766DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/ange.201607766/abstractPublisherArticle
ORCID:
AuthorORCID
Shi, Bing-Feng0000-0003-0375-955X
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.
Funders:
Funding AgencyGrant Number
National Basic Research Program of China2015CB856600
Natural Science Foundation of China21572201
Natural Science Foundation of China21422206
Subject Keywords:amino acids; asymmetric transformations; chiral auxiliaries; C-H activation; silylation
Record Number:CaltechAUTHORS:20161004-083417715
Persistent URL:http://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:02 Jun 2017 23:15

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