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Cinchona Alkaloid Amide Catalyzed Enantioselective Formal [2+2] Cycloadditions of Allenoates and Imines: Synthesis of 2,4‐Disubstituted Azetidines
Author(s) -
Denis JeanBaptiste,
Masson Géraldine,
Retailleau Pascal,
Zhu Jieping
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.201100706
Subject(s) - cinchona , enantioselective synthesis , amide , chemistry , catalysis , enantiomer , quinidine , alkyl , organic chemistry , cycloaddition , molecular sieve , alkaloid , combinatorial chemistry , pharmacology , medicine
Mix and go : The quinidine amide 1 catalyzed [2+2] cycloaddition between N ‐sulfonylimines 2 and alkyl 2,3‐butadienoates 3 afforded the R ‐configured azetidines 4 in excellent yields and enantioselectivities (M.S.=molecular sieve). The S enantiomer was obtained when a quinine amide catalyst, the pseudoenantiomer of 1 , was used.