Cinchona Alkaloid Amide Catalyzed Enantioselective Formal [2+2] Cycloadditions of Allenoates and Imines: Synthesis of 2,4‐Disubstituted Azetidines | Zendy

Denis JeanBaptiste | Zendy; Masson Géraldine | Zendy; Retailleau Pascal | Zendy; Zhu Jieping | Zendy

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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.

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