216690-18-5Relevant 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)
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 Asymmetric Hydrogenation of Tetrasubstituted Unsaturated Lactams: An Efficient Approach to Enantioenriched 3,4-Disubstituted Piperidines
Pan, Yingmin,Yin, Congcong,Yin, Qin,Zhang, Xumu
, p. 675 - 680 (2022/02/07)
Asymmetric hydrogenation of tetrasubstituted alkenes remains a formidable challenge in asymmetric catalysis. We report herein an unprecedented Rh-catalyzed enantioselective and diastereoselective hydrogenation of easily accessed α,β-disubstituted unsaturated lactams to afford synthetically valuable chiral lactams with 1,2-consecutive stereocenters. The reaction could be performed on the gram scale, and the products could be concisely transformed to enantiomerically pure trans-3,4-disubstituted piperidines, which are prevalent structural units in medicinal agents.
Enantioselective organocatalytic Michael addition of malonates to α,β-unsaturated aldehydes in water
Ma, Anqi,Zhu, Shaolin,Ma, Dawei
, p. 3075 - 3077 (2008/09/20)
The Michael addition of malonates to α,β-unsaturated aldehydes catalyzed by O-TMS protected diphenylprolinols and acetic acid in water occurs at 0 °C to rt. In most cases, the reaction runs to completion in less than 24 h. A wide range of aldehydes includ
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.