59859-58-4Relevant academic research and scientific papers
Highly Enantioselective Nickel-Catalyzed Intramolecular Hydroalkenylation of N- and O-Tethered 1,6-Dienes to Form Six-Membered Heterocycles
Li, Ke,Li, Mao-Lin,Zhang, Qi,Zhu, Shou-Fei,Zhou, Qi-Lin
, p. 7458 - 7461 (2018)
A highly enantioselective nickel-catalyzed intramolecular hydroalkenylation of N- or O-tethered 1,6-dienes was developed by using monodentate chiral spiro phosphoramidite ligands. The reaction provides an efficient and straightforward method for preparing very useful six-membered N- and O-heterocycles with high regioselectivity as well as excellent stereoselectivity from easily accessible starting materials under mild reaction conditions. The chiral spiro nickel catalyst developed in this study represents one of the few catalysts for highly enantioselective cyclization of unconjugated dienes.
Total Asymmetric Synthesis of (+)-Paroxetine and (+)-Femoxetine
Szcze?niak, Piotr,Buda, Szymon,Lefevre, Laura,Staszewska-Krajewska, Olga,Mlynarski, Jacek
, p. 6973 - 6982 (2019/11/20)
Total, asymmetric synthesis of (+)-Paroxetine and (+)-Femoxetine, selective serotonin reuptake inhibitors, used for the treatment of depression, anxiety, and panic disorders is reported. The key step is organocatalytic Michael addition of aldehydes to trans-nitroalkenes realized in bath or continues flow. High efficiency and selectivity in the Michael addition was achieved by application of Wang resin-supported Hayashi–J?rgensen catalyst.
Highly enantioselective organocatalytic cascade reaction for the synthesis of piperidines and oxazolidines
?íhalová, Sylva,Valero, Guillem,Schimer, Ji?í,Humpl, Marek,Dra?ínsky, Martin,Moyano, Albert,Rios, Ramon,Vesely, Jan
, p. 8942 - 8950 (2011/12/01)
The synthesis of piperidines and piperidines derivatives in enantiopure fashion has been a challenging goal for organic chemists. In this report we developed a nice cascade reaction for piperidine derivatives based in an amidomalonate Michael addition to enals followed by an intramolecular hemiaminal formation with good yields and enantioselectivities. Moreover we studied the 'in situ' intramolecular cyclization of this hemiaminals with alcohols forming fused piperidine-oxazolidines.
Asymmetric carbon-carbon bond formations in conjugate additions of lithiated N-Boc allylic and benzylic amines to nitroalkenes: Enantioselective synthesis of substituted piperidines, pyrrolidines, and pyrimidinones
Johnson, Timothy A.,Jang, Doo Ok,Slafer, Brian W.,Curtis, Michael D.,Beak, Peter
, p. 11689 - 11698 (2007/10/03)
(-)-Sparteine mediated lithiations of N-Boc-allylic and benzylic amines provide configurationally stable intermediates which on conjugate additions to nitroalkenes provide highly enantioenriched enecarbamate products in good yields, and with high diastere
Synthesis of Enantiopure trans-3,4-Disubstituted Piperidines. An Enantiodivergent Synthesis of (+)- And (-)-Paroxetine
Amat, Mercedes,Bosch, Joan,Hidalgo, Jose,Canto, Margalida,Perez, Maria,Llor, Nuria,Molins, Elies,Miravitlles, Carles,Orozco, Modesto,Luque, Javier
, p. 3074 - 3084 (2007/10/03)
Reaction of (R)-phenylglycinol with methyl 5-oxopentanoate gave either bicyclic lactam cis-1 (the kinetic product) or its isomer trans-1 (under equilibrating conditions) as the major products, which were converted to the corresponding (cis or trans) unsaturated lactams 4 and 5. On treatment with lithium alkyl (or aryl) cyanocuprates, these chiral building blocks undergo conjugate addition to give enantiopure trans-3,4-substituted 2-piperidone derivatives in high yield and stereoselectivity. The synthetic potential of this transformation is illustrated by the synthesis of (+)-femoxetine and the two enantiomers of the known antidepressant paroxetine.
Synthesis and 5HT modulating activity of stereoisomers of 3-phenoxymethyl-4-phenylpiperidines
Engelstoft, Mogens,Hansen, John Bondo
, p. 164 - 169 (2007/10/03)
A series of pairs of enantiomers of substituted 3-phenoxymethyl-4-phenylpiperidines has been prepared from arecoline or α-methylstyrene by a combination of stereospecific reactions and optical resolutions. The ability of the compounds to modulate serotonin (5HT) neurotransmission in vitro was determined. Several derivatives, among which is the antidepressant paroxetine, are very potent inhibitors of 5HT reuptake. These compounds exhibit a pronounced steric requirement for inhibition of 5HT reuptake and binding to 5HT2A and 5HT2C receptors. Acta Chemica Scandinavica 1996.
ON THE FORMATION OF THE 1-AZA-(3.1.1)-BICYCLOHEPTANE RING SYSTEM
Christensen, J. A.,Engelstoft, M.,Schaumburg, K.,Schou, H.,Watjen, F.
, p. 5151 - 5152 (2007/10/02)
The preveously unpublished bicyclic system 1-aza-(3.1.1)-biycyloheptane has been shown to exist as an unexpected intermediate in the synthesis of Femoxetine, a CNS active drug.
