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Asymmetric Organocatalytic Intramolecular Aza‐Michael Addition of Enone Carbamates: Catalytic Enantioselective Access to Functionalized 2‐Substituted Piperidines
Author(s) -
Liu JianDong,
Chen YingChun,
Zhang GuoBiao,
Li ZhiQiang,
Chen Peng,
Du JiYuan,
Tu YongQiang,
Fan ChunAn
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100282
Subject(s) - enantioselective synthesis , michael reaction , chemistry , moiety , enone , stereocenter , piperidine , organocatalysis , intramolecular force , ketone , combinatorial chemistry , organic chemistry , catalysis
The synthetically useful functionalized 2‐substituted piperidines containing a lateral ketone group have been strategically accessed via an organocatalytic enantioselective intramolecular aza‐Michael addition of enone carbamates, in which a novel internal substrate combination of the enone moiety as Michael acceptor and the carbamate moiety as Michael donor was revealed in asymmetric bifunctional organocatalysis. This heteroatom conjugate addition, which was realized by using a catalytic chiral Cinchona ‐based primary‐tertiary diamine and an achiral Brønsted acid, mostly proceeded in high yield and good to excellent stereocontrol (up to 99% ee ). This reaction provides an alternative catalytic asymmetric method for installing the stereogenic nitrogen‐containing carbon center in functionalized 2‐substituted piperidines, leading to the development of a straightforward and expeditious synthesis of some naturally occurring bioactive 2‐substituted piperidine alkaloids.