Divergent and Stereoselective Synthesis of β-Silyl-α-Amino Acids through Palladium-Catalyzed Intermolecular Silylation of Unactivated Primary and Secondary C−H Bonds
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.
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.Attached Files
Supplemental Material - ange201607766-sup-0001-misc_information.pdf
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Additional details
- Eprint ID
- 70789
- Resolver ID
- CaltechAUTHORS:20161004-083417715
- 2015CB856600
- National Basic Research Program of China
- 21572201
- Natural Science Foundation of China
- 21422206
- Natural Science Foundation of China
- Created
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2016-10-04Created from EPrint's datestamp field
- Updated
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2021-11-02Created from EPrint's last_modified field