297748-84-6

Upstream product

• 616-38-6 carbonic acid dimethyl ester 
• 177966-75-5 (4S)-1-(phenylmethyl)-4-(4-fluorophenyl)piperidin-2-one 
• 459-57-4 4-fluorobenzaldehyde 
• 63131-29-3 methyl 4-fluorobenzoyl acetate 
• 216690-16-3 (3R)-methyl hydrogen 3-(4-fluorophenyl)pentane-1,5-dioate 
• 216690-15-2 dimethyl 3-(4-fluorophenyl)glutarate 
• 297748-83-5 (S)-3-(4-Fluoro-phenyl)-5-hydroxy-pentanoic acid methyl ester 

Downstream Products

• 1057326-99-4 d4-[1-benzyl-4-(4-fluorophenyl)-piperidin-3-yl]-methanol 
• 130855-30-0 (+)-paroxetin 
• 105834-28-4 (-)trans-1-benzyl-4-(4-fluorophenyl)-3-(3,4-methylenedioxyphenoxymethyl)piperidine 
• 188869-25-2 (-)-trans-1-benzyl-3-hydroxymethyl-4-(4-fluorophenyl)piperidine 

Relevant academic research and scientific papers

Catalytic Asymmetric Hydrogenation of Tetrasubstituted Unsaturated Lactams: An Efficient Approach to Enantioenriched 3,4-Disubstituted Piperidines

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.

Synthesis of chiral lactams: Via asymmetric hydrogenation of α,β-unsaturated nitriles

A highly efficient Rh-catalyzed enantioselective hydrogenation of α,β-unsaturated nitriles containing ester/amide groups has been developed. Under mild conditions, with a complex of rhodium and (S,S)-f-spiroPhos as the catalyst, a variety of α,β-unsaturated nitriles bearing an ester or amide group were successfully hydrogenated to the corresponding chiral nitriles with excellent enantioselectivities (up to 99.7% ee) and high turnover numbers (TON = 10000). Furthermore, this catalyst system was also successfully applied to the synthesis of important chiral pharmacophore fragments, lactams, Paroxetine and amino acids.

Asymmetric synthesis of (-)-paroxetine using PLE hydrolysis

(-)-Paroxetine hydrochloride was produced asymmetrically in seven steps starting from 4-fluoro-benzaldehyde. The stereocenter at C-4 was initially set through desymmetrization of glutaric acid bis methyl ester 4 by PLE hydrolysis. A unique one-pot reduction-alkylation procedure was then developed to provide entry to lactam 2 with the appropriate absolute stereochemistry. (C) 2000 Elsevier Science Ltd.