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Enantioselective Synthesis of Chiral Imidazolidine Derivatives by Asymmetric Silver/Xing‐Phos‐Catalyzed Homo‐1,3‐Dipolar [3+2] Cycloaddition of Azomethine Ylides
Author(s) -
Yu Bo,
Bai XingFeng,
Lv JiYuan,
Yuan Yang,
Cao Jian,
Zheng ZhanJiang,
Xu Zheng,
Cui YuMing,
Yang KeFang,
Xu LiWen
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700732
Subject(s) - enantioselective synthesis , imidazolidine , stereocenter , chemistry , cycloaddition , bifunctional , 1,3 dipolar cycloaddition , catalysis , ligand (biochemistry) , combinatorial chemistry , stereochemistry , organic chemistry , receptor , biochemistry
Enantioselective synthesis of chiral heterocyclic derivatives is an important and challenging topic in the field of synthetic chemistry. In this work, the first stereocontrolled dimerization‐type homo‐1,3‐dipolar [3+2] cycloaddition reaction of glycine aldimino esters for creating new heterocycles bearing multiple stereogenic centers has been developed through chiral phosphine ligand‐involved silver catalysis. A variety of chiral imidazolidines could be obtained with high yields and good diastereoselectivities as well as excellent enantioselectivities by employing Xing‐Phos as chiral phosphorus ligand. In addition, the silver/Xing‐Phos‐catalyzed homo‐1,3‐dipolar [3+2] cycloaddition reaction is also a facile and novel protocol for catalytic polymerization of bifunctional glycine aldimino esters to give chiral poly(imidazolidine)s with a very narrow molecular weight distribution.