Amine‐Promoted Asymmetric (4+2) Annulations for the Enantioselective Synthesis of Tetrahydropyridines: A Traceless and Recoverable Auxiliary Strategy | Zendy

Hu Pengfei | Zendy; Hu Jian | Zendy; Jiao Jiajun | Zendy; Tong Xiaofeng | Zendy

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Amine‐Promoted Asymmetric (4+2) Annulations for the Enantioselective Synthesis of Tetrahydropyridines: A Traceless and Recoverable Auxiliary Strategy

Author(s) -

Hu Pengfei,

Hu Jian,

Jiao Jiajun,

Tong Xiaofeng

Publication year - 2013

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.201300526

Subject(s) - enantioselective synthesis , amine gas treating , trace (psycholinguistics) , combinatorial chemistry , computer science , chemistry , service (business) , information retrieval , world wide web , organic chemistry , catalysis , business , linguistics , philosophy , marketing

Gone, without a trace : The in situ reaction of 2‐(acetoxymethyl)buta‐2,3‐dienoate and a secondary amine produces a 2‐methylene‐3‐oxobutanoate equivalent that can be used in asymmetric [4+2] annulations with N ‐tosylimines to provide tetrahydropyridines in good to excellent yields and enantioselectivities. The amine is easily recovered and acts as a traceless auxiliary.

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