177966-75-5

Upstream product

• 100-46-9 benzylamine 
• 63131-29-3 methyl 4-fluorobenzoyl acetate 
• 100-39-0 benzyl bromide 
• 459-57-4 4-fluorobenzaldehyde 
• 3449-63-6 3-(4-fluorophenyl)pentan-1,5-dioic acid 
• 1130247-01-6 (3'R,4S)-5,5-di(2-methoxy-5-methylphenyl)-3-[3-(4-fluorophenyl)-4-methoxycarbonyl-1-oxobutyl]-4-isopropyloxazolidin-2-one 
• 4926-12-9 4-(4-fluorophenyl)dihydropyran-2,6(3H)-dione 
• 52927-40-9 dimethyl 2-(4-fluorobenzylidene)malonate 
• 216690-16-3 (3R)-methyl hydrogen 3-(4-fluorophenyl)pentane-1,5-dioate 
• 297748-83-5 (S)-3-(4-Fluoro-phenyl)-5-hydroxy-pentanoic acid methyl ester 
• 1765-93-1 4-fluoroboronic acid 
• 128773-72-8 1‐benzyl‐5,6‐dihydropyridin‐2(1H)‐one 
• 511283-91-3 1-(phenylmethyl)-4-(4-fluorophenyl)piperidin-2,6-dione 

Downstream Products

• 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 
• 297748-84-6 (3R,4S)-methyl-1-benzyl-4-(4-fluorophenyl)-2-oxopiperidine-3-carboxylate 

Relevant academic research and scientific papers

Rhodium-catalyzed asymmetric 1,4-addition of organoboron reagents to 5,6-dihydro-2(1H)-pyridinones. Asymmetric synthesis of 4-aryl-2-piperidinones

Catalytic asymmetric synthesis of 4-aryl-2-piperidinones was realized for the first time by asymmetric 1,4-addition of arylboron reagents to 5,6-dihydro-2(1H)-pyridinones in the presence of a chiral bisphosphine-rhodium catalyst. In the reaction introduci

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.

Enantioselective Desymmetrization of Glutarimides Catalyzed by Oxazaborolidines Derived from cis-1-Amino-indan-2-ol

Enantioselective reductive desymmetrization of glutarimides has been achieved employing an oxazaborolidine catalyst derived from cis-1-amino-indan-2-ol. The reaction was found to proceed through a stereoablative process that upgraded the enantioselectivity of an intermediate hydroxy-lactam. The reaction was generally tolerant of a number of substituents in the 4-position, giving enantiomeric excesses of greater than 82%.

An enantiodivergent and formal synthesis of paroxetine enantiomers by asymmetric desymmetrization of 3-(4-fluorophenyl)glutaric anhydride with a chiral SuperQuat oxazolidin-2-one

The asymmetric desymmetrization of 3-(4-fluorophenyl)glutaric anhydride 9 with lithiated chiral oxazolidin-2-one 8 has been studied. The desymmetrized product was formed with >90% de and converted into known intermediates for both (+)- and (-)-paroxetines.

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.