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Pd/Cu dual catalysis: highly enantioselective access to α-substituted α-amino acids and α-amino amides
Chemical Communications ( IF 4.9 ) Pub Date : 2017-12-11 00:00:00 , DOI: 10.1039/c7cc08732b
Xiaohong Huo 1, 2, 3, 4, 5 , Jingke Fu 1, 2, 3, 4, 5 , Xiaobo He 1, 2, 3, 4, 5 , Jianzhong Chen 1, 2, 3, 4, 5 , Fang Xie 1, 2, 3, 4, 5 , Wanbin Zhang 1, 2, 3, 4, 5
Affiliation  

The asymmetric allylation of glycine iminoesters has been accomplished through a synergistic Pd/Cu catalyst system, affording a range of α-substituted α-amino acids in high yields and with excellent enantioselectivities (88 → 99% ee). The introduction of a Cu-P,N-metallocenyl complex-activated glycine iminoester to the chiral palladium-catalyzed allylic allylation process is crucial owing to its high reactivity and excellent enantioselectivities. Importantly, this Pd/Cu dual catalysis strategy can be used for the asymmetric allylic alkylation of prochiral glycine amide derivatives, which could be further utilized to synthesize biologically important vicinal diamines.

中文翻译:

Pd / Cu双重催化:高度对映选择性地获得α-取代的α-氨基酸和α-氨基酰胺

甘氨酸亚氨基酸酯的不对称烯丙基化是通过协同的Pd / Cu催化剂体系完成的,以高收率和优异的对映选择性(88→99%ee)提供了一系列α-取代的α-氨基酸。由于其高反应性和优异的对映选择性,将Cu- PN-金属茂基复合物活化的甘氨酸亚氨基酯引入手性钯催化的烯丙基烯丙基化过程是至关重要的。重要的是,该Pd / Cu双重催化策略可用于前手性甘氨酸酰胺衍生物的不对称烯丙基烷基化,其可进一步用于合成生物学上重要的邻位二胺。
更新日期:2018-01-16
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