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Catalytic Asymmetric Construction of Quaternary α‐Amino Acid Containing Pyrrolidines through 1,3‐Dipolar Cycloaddition of Azomethine Ylides to α‐Aminoacrylates
Author(s) -
Wang Zheng,
Luo Shuai,
Zhang Shoude,
Yang WuLin,
Liu YangZi,
Li Honglin,
Luo Xiaoyan,
Deng WeiPing
Publication year - 2013
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.201300204
Subject(s) - cycloaddition , catalysis , chemistry , enantioselective synthesis , azomethine ylide , 1,3 dipolar cycloaddition , amino acid , combinatorial chemistry , stereochemistry , organic chemistry , medicinal chemistry , biochemistry
The first catalytic enantioselective 1,3‐dipolar cycloaddition of azomethine ylides to α‐aminoacrylate catalyzed by a AgOAc/ferrocenyl oxazolinylphosphine (FOXAP) system was developed, which exhibits excellent exo‐ and enantioselectivity (92–99 % ee ). This process provides efficient access to useful 4‐aminopyrrolidine‐2,4‐dicarboxylic acid (APDC)‐like compounds containing a unique quaternary α‐amino acid unit.