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Organocatalytic Asymmetric Inverse‐Electron‐Demand Aza‐Diels–Alder Reaction of N ‐Sulfonyl‐1‐aza‐1,3‐butadienes and Aldehydes
Author(s) -
Han Bo,
Li JunLong,
Ma Chao,
Zhang ShanJun,
Chen YingChun
Publication year - 2008
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.200804183
Subject(s) - chemistry , sulfonyl , hemiaminal , inverse , combinatorial chemistry , derivative (finance) , organic chemistry , mathematics , business , alkyl , geometry , finance
Water is crucial for high transformation efficiency in the title reaction catalyzed by the α,α‐diphenylprolinol derivative 1 . Excellent stereoselectivities were observed for a broad spectrum of substrates (see scheme; TMS=trimethylsilyl, Tos= p ‐toluenesulfonyl). A diverse range of chiral piperidine derivatives and other valuable compounds can be prepared from the hemiaminal products.