Premium
Asymmetric Inverse‐Electron‐Demand 1,3‐Dipolar Cycloaddition of C,N‐Cyclic Azomethine Imines: An Umpolung Strategy
Author(s) -
Hashimoto Takuya,
Omote Masato,
Maruoka Keiji
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201100331
Subject(s) - umpolung , cycloaddition , inverse , stereoselectivity , chemistry , electron , combinatorial chemistry , computer science , computational chemistry , organic chemistry , catalysis , mathematics , physics , nucleophile , quantum mechanics , geometry
Oompa loompa : The title reaction has been accomplished with high stereoselectivity by use of an axially chiral dicarboxylic acid (see scheme). Employment of vinylogous aza‐enamines as novel dipolarophiles was also implemented to establish a new concept of the inverse‐electron‐demand umpolung 1,3‐dipolar cycloaddition. Bz=benzoyl, EDG=electron‐donating group.