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Synergistic Cu/Pd‐Catalyzed Asymmetric Allenylic Alkylation of Azomethine Ylides for the Construction of α‐Allene‐Substituted Nonproteinogenic α‐Amino Acids
Author(s) -
Liu HuaChao,
Hu YuanZheng,
Wang ZuoFei,
Tao HaiYan,
Wang ChunJiang
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201901046
Subject(s) - catalysis , allene , chemistry , imine , combinatorial chemistry , alkylation , amino acid , enantioselective synthesis , substrate (aquarium) , organic chemistry , stereochemistry , biochemistry , oceanography , geology
An unprecedented asymmetric allenylic alkylation of readily available imine esters, which was enabled by a synergistic Cu/Pd catalysis, has been developed. This dual catalytic system possesses good substrate compatibility, delivering a diverse array of nonproteinogenic α‐allenylic α‐mono‐ or α,α‐disubstituted α‐amino acids (α‐AAs) with high yields and generally excellent enantioselectivities. Furthermore, the scalability and practicability of the current synthetic protocol were proven by performing gram‐scale reactions and by the first catalytic asymmetric synthesis of naturally occurring ( S )‐γ‐allenic α‐amino acid, respectively.