201855-60-9Relevant articles and documents
Multigram-scale flow synthesis of the chiral key intermediate of (-)-paroxetine enabled by solvent-free heterogeneous organocatalysis
?tv?s, Sándor B.,Pericàs, Miquel A.,Kappe, C. Oliver
, p. 11141 - 11146 (2019/12/28)
The catalytic enantioselective synthesis of the chiral key intermediate of the antidepressant (-)-paroxetine is demonstrated as a continuous flow process on multi-gram scale. The critical step is a solvent-free organocatalytic conjugate addition followed
Catalytic Michael/Ring-Closure Reaction of α,β-Unsaturated Pyrazoleamides with Amidomalonates: Asymmetric Synthesis of (?)-Paroxetine
Zhang, Yu,Liao, Yuting,Liu, Xiaohua,Yao, Qian,Zhou, Yuhang,Lin, Lili,Feng, Xiaoming
, p. 15119 - 15124 (2016/10/11)
A highly enantioselective tandem Michael/ring-closure reaction of α,β-unsaturated pyrazoleamides and amidomalonates has been accomplished in the presence of a chiral N,N′-dioxide–Yb(OTf)3complex (Tf: trifluoromethanesulfonyl) to give various substituted chiral glutarimides with high yields and diastereo- and enantioselectivities. Moreover, this methodology could be used for gram-scale manipulation and was successfully applied to the synthesis of (?)-paroxetine. Further nonlinear and HRMS studies revealed that the real catalytically active species was a monomeric L-PMe2–Yb3+complex. A plausible transition state was proposed to explain the origin of the asymmetric induction.
Optically pure γ-butyrolactones and epoxy esters via two stereocentered HKR of 3-substituted epoxy esters: A formal synthesis of (-)-paroxetine, Ro 67-8867 and (+)-eldanolide
Devalankar, Dattatray A.,Karabal, Pratibha U.,Sudalai, Arumugam
, p. 1280 - 1285 (2013/05/08)
The HKR of racemic anti- or syn-3-substituted epoxy esters catalyzed by a Co(iii)salen complex provides ready access to the corresponding enantioenriched 3,4-disubstituted γ-butyrolactones and 3-substituted epoxy esters. This strategy has been successfully employed in the formal synthesis of biologically active 3,4-disubstituted piperidine derivatives, (-)-paroxetine and Ro 67-8867 and a natural product, (+)-eldanolide.
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
scheme or table, 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.
Stereospecific construction of substituted piperidines. Synthesis of (-)-paroxetine and (+)-laccarin
Bower, John F.,Riis-Johannessen, Thomas,Szeto, Peter,Whitehead, Andrew J.,Gallagher, Timothy
, p. 728 - 730 (2007/10/03)
Short and efficient enantioselective syntheses of (-)-paroxetine and (+)-laccarin are described based on the highly stereospecific cleavage of C(3)-substituted 1,3-cyclic sulfamidates. The Royal Society of Chemistry.
Organocatalytic conjugate addition of malonates to α,β- unsaturated aldehydes: Asymmetric formal synthesis of (-)-paroxetine, chiral lactams, and lactones
Brandau, Sven,Landa, Aitor,Franzen, Johan,Marigo, Mauro,Jorgensen, Karl Anker
, p. 4305 - 4309 (2007/10/03)
(Chemical Equation Presented) In addition: The scope of the title reaction is demonstrated by the synthesis of chiral lactones and lactams. The latter class of compounds is very important for the preparation of the pharmaceutical compounds such as (-)-par
Concise synthesis of trans- and cis-3,4-disubstituted piperidines based on regio- and stereoselective allylation of cyclopentenyl esters
Igarashi, Junji,Ishiwata, Hiroyuki,Kobayashi, Yuichi
, p. 8065 - 8068 (2007/10/03)
3,4-Disubstituted piperidines were synthesized through anti S N2′ allylation of 4-substituted 2-cyclopentenyl esters with reagents based on RMgX and CuX, thus allowing equal access to both trans- and cis-isomers. As an application, the paroxeti
Application of the chiral base desymmetrisation of imides to the synthesis of the alkaloid jamtine and the antidepressant paroxetine
Gill, Christopher D.,Greenhalgh, Daniel A.,Simpkins, Nigel S.
, p. 9213 - 9230 (2007/10/03)
The synthesis of the alkaloid jamtine and the antidepressant paroxetine have been addressed by a strategy involving asymmetric desymmetrisation of prochiral imides by a chiral lithium amide base. A short reaction sequence, starting with a cyclohexane fused succinimide, led to the structures originally reported for the alkaloid jamtine and its derived N-oxide. The structures synthesised are shown not to correspond with those originally reported. A second sequence involves desymmetrisation of a 4-arylglutarimide, and provides a short enantioselective synthesis of the drug substance paroxetine.
A formal synthesis of (-)-paroxetine by enantioselective ring enlargement of a trisubstituted prolinol
Cossy, Janine,Mirguet, Olivier,Pardo, Domingo Gomez,Desmurs, Jean-Roger
, p. 3543 - 3551 (2007/10/03)
A ring expansion and a radical dehalogenation have been used as the key steps in a formal total synthesis of (-)-paroxetine. The substituted piperidine ring precursor of (-)-paroxetine was generated by means of a stereoselective ring expansion of prolinol. ( Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).
Ring expansion: Formal total synthesis of (-)-paroxetine
Cossy, Janine,Mirguet, Olivier,Gomez Pardo, Domingo,Desmurs, Jean-Roger
, p. 5705 - 5707 (2007/10/03)
A ring expansion and a radical dehalogenation have been used as the key steps in a formal total synthesis of (-)-paroxetine. A stereoselective ring expansion of prolinol generated the substituted piperidine ring precursor of (-)-paroxetine.
