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
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通过 Pd/Cu 双催化对氨基酸和小肽进行立体选择性和位点特异性烯丙基烷基化

DOI:
10.1021/jacs.7b05460
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发表时间:
2017-07-26
影响因子:
15
通讯作者:
Zhang, Wanbin
Zhang, Wanbin
中科院分区:
化学1区
文献类型:
--
作者:
Huo, Xiaohong;He, Rui;Zhang, Wanbin

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本文报道了一种立体选择性和位点特异性的席夫碱活化氨基酸和小肽的烯丙基烷基化反应。一系列非编码的α,α-二烷基α-氨基酸容易以高产率和优异的对映选择性(高达> 99%ee)合成。此外,直接和高度立体选择性合成的小肽与对映体纯的α-烷基或α,α-二烷基α-氨基酸残基掺入在特定的网站上使用这种双催化剂系统完成。
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 alpha,alpha-dialkyl alpha-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 alpha-alkyl or alpha,alpha-dialkyl alpha-amino acids residues incorporated at specific sites was accomplished using this dual catalyst system.