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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.