164732-66-5Relevant academic research and scientific papers
Substituted Dihydropyridine Synthesis by Dearomatization of Pyridines
Fliege, Julian,Glorius, Frank,Heusler, Arne,Wagener, Tobias
supporting information, p. 13793 - 13797 (2021/05/13)
Dearomatization is an effective method to transform readily available N-heterocycles into partially saturated motifs. Manipulation of dihydro-derivatives holds great potential and provides access to a variety of semi-saturated N-heterocyclic building blocks. However, current strategies are limited in scope and the use of sensitive reagents restricts the applicability in synthetic laboratories. Herein, we report the synthesis of a broad variety of N-substituted 1,4- and 1,2-dihydropyridines by very mild and selective reduction with amine borane for the first time.
?-C(sp2)-H alkylation of enamides using xanthate chemistry
Bertho, Sylvain,Dondasse, Isma?l,Retailleau, Pascal,Nicolas, Cyril,Gillaizeau, Isabelle
supporting information, p. 7129 - 7141 (2020/05/16)
Access to the ?-amino-?,?-unsaturated acyl scaffold was established by applying xanthate chemistry to enamides. This original ?-C(sp2)-H alkylation is regioselective and exhibits broad substrate scope and good functional group tolerance. The la
Diastereoselective synthesis of 3-fluoro-2-substituted piperidines and pyrrolidines
Gichuhi, Paul N.,Kuriyama, Masami,Onomura, Osamu
, p. 331 - 346 (2014/01/17)
A facile procedure for synthesis of trans-3-fluoro-2-substituted piperidines by utilizing electrophilic fluorination of cyclic enamines and Lewis acid mediated nucleophilic substitution has been developed. Also, optically active trans-2-allyl-3-fluorinate
Concise asymmetric synthesis of (+)-febrifugine utilizing trans-selective intramolecular conjugate addition
Sukemoto, Satoshi,Oshige, Miyo,Sato, Masahiro,Mimura, Ken-Ichiro,Nishioka, Hiromi,Abe, Hitoshi,Harayama, Takashi,Takeuchi, Yasuo
experimental part, p. 3081 - 3087 (2009/04/07)
Intramolecular conjugate addition of γ-substituted (E)- α,β-unsaturated ketones with a Lewis acid (BF3· OEt2) selectively afforded trans-2,3-disubstituted piperidine derivatives. Chiral substrates were synthesized by Sharpless asymmetric dihydroxylation of the enamine; the antimalarial compound febrifugine was synthesized from the major product of the conjugate addition reaction. Georg Thieme Verlag Stuttgart.
Highly enantioselective introduction of bis(alkoxycarbonyl)methyl group into the 2-position of piperidine skeleton
Matsumura, Yoshihiro,Minato, Diashirou,Onomura, Osamu
, p. 654 - 663 (2008/02/06)
Copper ion catalyzed carbon-carbon bond forming reaction of N-acyliminium ions with diaryl malonates was achieved with high enantioselectivity. The key intermediates in the method were 2-methoxy-3,4-didehydropiperidines, which were easily prepared through
Palladium-catalyzed coupling of vinyl phosphates with aryl or heteroaryl boronic acids. Application to the synthesis of substituted nitrogen containing heterocycles
Lepifre, Franck,Clavier, Sylvain,Bouyssou, Pascal,Coudert, Gérard
, p. 6969 - 6975 (2007/10/03)
Substituted nitrogen-containing heterocycles were prepared in three steps from commercially available derivatives via an extension of the Suzuki reaction involving the palladium-catalyzed coupling of vinyl phosphates with aryl or heteroaryl boronic acids.
Reactivity of 2-Cyano-1,4,5,6-tetrahydro-1-pyridinecarboxylic Acid Esters Towards Various Nucleophiles: Regio- and Stereoselectivity of the Attack
Stanetty,Mihovilovic,Mereiter
, p. 1061 - 1072 (2007/10/03)
The synthesis and reactivity of the title compounds towards nucleophiles are discussed. The regio- and diastereoselectivity of the attack is highly dependent on the carbamic ester and the type of nucleophile applied. Both Michael type addition across the
