Premium
A Concise Assembly of Electron‐Deficient 2,4‐Dienes and 2,4‐Dienals: Regio‐ and Stereoselective exo ‐Diels–Alder and Redox Reactions through Sequential Amine and Carbene Catalysis
Author(s) -
Ma Chao,
Jia ZhiJun,
Liu JingXin,
Zhou QingQing,
Dong Lin,
Chen YingChun
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.201208349
Subject(s) - regioselectivity , carbene , alkene , chemistry , stereoselectivity , catalysis , redox , hydride , aldehyde , amine gas treating , cycloaddition , organic chemistry , hydrogen
Ideal relay catalysis : A γ,δ‐regioselective anomalous exo ‐Diels–Alder reaction with electron‐deficient β‐substituted 2,4‐dienes and 2,4‐dienals has been developed by using trienamine activation. The resulting multifunctional cycloadducts contain perfectly positioned functional groups, thereby facilitating a 1,5‐hydride transfer from the C–H group of an aldehyde to an activated alkene under sequential catalysis of a carbene (see scheme).