Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Stereoselective and Site-Specific Allylic Alkylation of Amino Acids and Small Peptides via a Pd/Cu Dual Catalysis

Stereoselective and Site-Specific Allylic Alkylation of Amino Acids and Small Peptides via a Pd/Cu Dual Catalysis
Jingke Fu, Guoqiang Yang, Xiaohong Huo, Wanbin Zhang, Jiacheng Zhang, Rui He
We report a stereoselective and site-specific allylic alkylation of Schiff base activated amino acids and small peptides via a Pd/Cu dual catalysis. A range of noncoded α,α-dialkyl α-amino acids were easily synthesized in high yields and with excellent enantioselectivities (up to >99% ee). Furthermore, a direct and highly stereoselective synthesis of small peptides with enantiopure α-alkyl or α,α-dialkyl α-amino acids residues incorporated at specific sites was accomplished using this dual catalyst system.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b05460

DOI: 10.1021/jacs.7b05460

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