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Titanocene(III)‐Catalyzed Three‐Component Reaction of Secondary Amides, Aldehydes, and Electrophilic Alkenes
Author(s) -
Zheng Xiao,
He Jiang,
Li HengHui,
Wang Ao,
Dai XiJie,
Wang AiE,
Huang PeiQiang
Publication year - 2015
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.201506907
Subject(s) - electrophile , catalysis , component (thermodynamics) , chemistry , aldehyde , organic chemistry , medicinal chemistry , physics , thermodynamics
An umpolung Mannich‐type reaction of secondary amides, aliphatic aldehydes, and electrophilic alkenes has been disclosed. This reaction features the one‐pot formation of CN and CC bonds by a titanocene‐catalyzed radical coupling of the condensation products, from secondary amides and aldehydes, with electrophilic alkenes. N‐substituted γ‐amido‐acid derivatives and γ‐amido ketones can be efficiently prepared by the current method. Extension to the reaction between ketoamides and electrophilic alkenes allows rapid assembly of piperidine skeletons with α‐amino quaternary carbon centers. Its synthetic utility has been demonstrated by a facile construction of the tricyclic core of marine alkaloids such as cylindricine C and polycitorol A.