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Asymmetric Three‐Component Inverse Electron‐Demand Aza‐Diels–Alder Reaction: Efficient Synthesis of Ring‐Fused Tetrahydroquinolines
Author(s) -
Xie Mingsheng,
Chen Xiaohong,
Zhu Yin,
Gao Bo,
Lin Lili,
Liu Xiaohua,
Feng Xiaoming
Publication year - 2010
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.201000590
Subject(s) - stereocenter , ring (chemistry) , chemistry , cyclopentadiene , scandium , diels–alder reaction , component (thermodynamics) , organic chemistry , combinatorial chemistry , enantioselective synthesis , catalysis , physics , thermodynamics
Diels or no Diels : The titled reaction of aldehydes, anilines, and cyclopentadiene, promoted by 0.5–5 mol % of an N , N′ ‐dioxide scandium complex, afforded ring‐fused tetrahydroquinolines that contained three contiguous stereocenters. The one‐pot reaction delivers the products with good yields and excellent diastereo‐ and enantioselectivities.