37088-65-6

Upstream product

• 145774-23-8 (R)-1-hydroxymethyl-4-phenyl-2-azetidinone 
• 5661-55-2 4-phenylazetidin-2-one 
• 1271792-62-1 methyl (2Z)-3-(benzylamino)-3-phenylprop-2-enoate 
• 97-72-3 2-Methylpropionic anhydride 
• 67-56-1 methanol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 110425-62-2 N-(2-chloroacetyl)-4-phenylazetidin-2-one 
• 100-42-5 styrene 
• 1514926-95-4 1-(8-quinolinyl)-4-phenyl-azetidinone 
• 150884-50-7 benzaldehyde N-boc imine 
• 98-86-2 acetophenone 
• 614-27-7 methyl 3-oxo-3-phenylpropionate 
• 145694-38-8 4-phenyl-1-propionyloxymethyl-2-azetidinone 
• 74536-07-5 1-hydroxymethyl-4-phenyl-2-azetidinone 

Downstream Products

• 145148-37-4 (R)-1-(tert-Butyl-dimethyl-silanyl)-4-phenyl-azetidin-2-one 
• 120420-11-3 N-t-butyldimethylsilyl-3-methyl-4-phenylazetidin-2-one 
• 1067647-04-4 C₁₄H₁₇NO₃ 
• 872726-33-5 CP 99994 dihydrochloride 
• 145212-92-6 (2S,3S)-3-Amino-2-phenyl-piperidine-1-carboxylic acid benzyl ester 
• 145148-38-5 (3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-(3-chloro-propyl)-4-phenyl-azetidin-2-one 
• 145148-36-3 (S)-2-((R)-Amino-phenyl-methyl)-5-chloro-pentanoic acid methyl ester 
• 145212-91-5 methyl (2R,3S)-cis-2-phenylpiperidine-3-carboxylate 

Relevant academic research and scientific papers

Synthesis of chiral β-aminomalonates from 2-chlorotetrafluoroethanesulfinyl aldimines through the mannich reaction

An efficient method for the synthesis of chiral β-aminomalonates in good yields and with high diastereoselectivities was achieved through Mannich reactions between 2-chlorotetrafluoroethanesulfinyl aldimines and dialkyl malonates in the presence of N-trim

Asymmetric synthesis of β-lactam via palladium-catalyzed enantioselective intramolecular c(sp3)-h amidation

β-Lactams are important scaffolds in drug design and frequently used as reactive intermediates in organic synthesis. Catalytic reactions featuring intramolecular C-H amidation of alkyl carboxamide substrates could provide a straightforward disconnection strategy for β-lactam synthesis. Herein, we report a streamlined method for asymmetric synthesis of β-aryl β-lactams from propanoic acid and aryl iodides via Pd-catalyzed sequential C(sp3)-H functionalization. The lactam-forming reaction provides an example of PdII-catalyzed enantioselective intramolecular C(sp3)-H amidation reaction and proceeds up to 94% ee. The use of a 2-methoxy-5-chlorophenyl iodide oxidant is critical to control the competing reductive elimination pathways of the PdIV intermediate to achieve the desired chemoselectivity. Mechanistic studies suggest that both steric and electronic effects of the unconventional aryl iodide oxidant are responsible for controlling the competing C-N versus C-C reductive elimination pathways of the PdIV intermediate.

HPLC enantioseparation on a homochiral MOF-silica composite as a novel chiral stationary phase

The last frontier in the development of chiral stationary phases for chromatographic enantioseparation involves homochiral metal-organic frameworks (MOFs). Using enantiopure (R)-2,2′-dihydroxy-1,1′-binaphthalene-6,6′-dicarboxylic acid as a starting material, we prepared three homochiral MOFs that were further used as chiral stationary phases for high-performance liquid chromatography to separate the enantiomers of various kinds of racemic sulfoxides, sec-alcohols, β-lactams, benzoins, flavanones and epoxides. The experimental results showed excellent performances for enantioseparation, and highlighted that enantioseparation on homochiral MOF columns is practical.

Studies on N-activation for the lipase-catalyzed enantioselective preparation of β-amino esters from 4-phenylazetidin-2-one

The effect of N-substitution was examined for the enantio-selective lipase-catalyzed ring-opening reaction of racemic 4-phenylazetidin-2-one with methanol in dry organic solvents. Marked differences in the reactivity of various N-protected 4-phenylazetidin-2-ones were observed. Preparativescale reactions with Candida antarctica lipase B (Novozym 435 preparation) yielded N-acylated methyl (R)-3-amino-3- phenylpropanoates with enantiomeric excess (ee) values >99% in up to a 49% isolated yield, whereas Thermomyces lanuginosus lipase (Lipozyme TM IM) gave enantiomerically enriched methyl (S)-3-acetamido-3-phenylpropanoate. Candida antarctica lipase A catalyzed the cleavage of the N-chloroacetyl protective group, whereas all of the other examined lipases underwent the ring-opening reaction.

Homochiral coordination polymers with nanotubular channels for enantioselective sorption of chiral guest molecules

Two novel chiral coordination polymers were synthesized by treating C 2-symmetric 2,2′-dihydroxy- and 2,2′-dimethoxy-1, 1′-binaphthalene-3,3′-dicarboxylic acids with Cu2+, in which sorption of some chiral β-lactam compounds in the fr

METHOD FOR PRODUCING beta-AMINOCARBONYL COMPOUND

An optically active β-aminocarbonyl compound is obtained by a Mannich reaction between an aldimine in which: nitrogen is protected and a malonic acid diester, in the presence of optically active BINOL and dialkyl magnesium (in which two alkyl groups are the same or different) in an amount 1 to 2 molar times the amount of the BINOL.

Kinetic resolution of β-lactams via enantioselective N-acylation

Enantioselective N-acylation of 4-aryl-β-lactams in the presence of acyl transfer catalyst Cl-PIQ provides an effective method for their non-enzymatic kinetic resolution.

Triclorosilane-mediated stereoselective synthesis of β-amino esters and their conversion to highly enantiomerically enriched β-lactams

A highly stereoselective trichlorosilane-mediated reduction of N-benzyl enamines was developed; the combination of a low cost, easy to make metal-free catalyst and an inexpensive chiral auxiliary allowed to perform the reaction on substrates with different structural features often with total control of the stereoselectivity. By easy deprotection through hydrogenolysis followed by conversion of β-aminoester to 2-azetidinones, the synthesis of enantiomerically pure β-lactams (>98% e.e.) was successfully accomplished.

Magnesium(II)-binaphtholate as a practical chiral catalyst for the enantioselective direct mannich-type reaction with malonates

(Equation Presented). A highly enantioselective direct Mannich-type reaction of aldimines with dialkyl malonates was developed with the use of a Mg(II)-BINOLate salt, which was designed as a cooperative acid-base catalyst that can activate both aldimines and malonates. Optically active β-aminoesters and α-halo-β-aminoesters could be synthesized in high yields and with high enantioselectivities. This inexpensive and practical Mg(II)-BINOLate salt could be used in gram-scale catalysis.

Highly practical BINOL-derived acid-base combined salt catalysts for the asymmetric direct mannich-type reaction

The catalytic asymmetric direct Mannich-type reaction between aldimines and 1,3-dicarbonyl compounds is one of the most important carbon-carbon bond-forming reactions in organic chemistry. The resulting Mannich adducts can be efficiently transformed into pharmaceutically useful, optically active -amino ketones, -amino esters, -lactams, etc. In the course of our study of chiral acid-base combined salt catalysts for asymmetric reactions, we developed a series of simple, practical, chiral BINOL-derived salt catalysts, such as chiral pyridinium 1,1-binaphthyl-2,2-disulfonates 1, chiral lithium(I) binaphtholate 2, chiral magnesium(II) binaphtholate (3), chiral calcium(II) phosphate 4, and chiral phosphoric acid 5, which were particularly effective for direct Mannich-type reactions. 1 Introduction 2 1,1-Binaphthyl-2,2-disulfonic Acid (BINSA)-Pyridinium Salts 3 Lithium(I) Binaphtholate Salts 4 Magnesium(II) Binaphtholate Salts 5 Calcium(II) Phosphate Salts and Chiral Phosphoric Acids 6 Conclusions. Georg Thieme Verlag Stuttgart · New York.