876269-37-3

Upstream product

• 1603-79-8 phenylglyoxylic acid ethyl ester 
• 75-52-5 nitromethane 

Downstream Products

• 876269-48-6 (S)-3-Azido-2-hydroxy-2-phenyl-propionic acid ethyl ester 
• 99986-48-8 3-Amino-2-hydroxy-2-phenyl-propionsaeure-aethylester 

Relevant academic research and scientific papers

Anti-Selective Catalytic Asymmetric Nitroaldol Reaction of α-Keto Esters: Intriguing Solvent Effect, Flow Reaction, and Synthesis of Active Pharmaceutical Ingredients

A rare-earth metal/alkali metal bimetallic catalyst proved particularly effective for enantioselectively coupling nitroalkanes and α-keto esters in an anti-selective manner to afford synthetically versatile, densely functionalized, and optically active α-nitro tertiary alcohols. A chiral diamide ligand captured two distinct metal cations, giving rise to a catalytically competent solid-phase heterobimetallic catalyst by simple mixing via self-assembly. The advantage of the solid-phase asymmetric catalyst was realized by successful application to the enantio- and diastereoselective reaction in a continuous-flow platform. The use of closely related solvents in terms of structures and polarity parameters, THF and its methylated congener 2-Me-THF, had an unexpectedly large solvent effect both on the reaction rate and the stereoselectivity. The nitroaldol products share a privileged unit for active pharmaceutical ingredients, as demonstrated by the streamlined enantioselective synthesis of the marketed antifungal agents efinaconazole and albaconazole.

Catalytic enantioselective Henry reaction of α-keto esters, 2-acylpyridines and 2-acylpyridine: N -oxides

A pre-prepared Ni-PyBisulidine complex has been developed for the catalytic asymmetric Henry reaction of α-keto esters, 2-acylpyridines and 2-acylpyridine N-oxides. The corresponding β-nitro-α-hydroxy esters were obtained in good to excellent yields (up t

Dynamic control over catalytic function using responsive bisthiourea catalysts

Two novel bisthiourea molecular motor-based catalysts were designed and their dynamic control of activity and stereoselectivity in the Henry reaction using heat and light as external stimuli was investigated. Enantioselective organocatalysis studies established that a basic functional group is not required within the catalyst core to effect efficient dual stereocontrol, illustrating novel stimuli responsive organocatalysts.

Enantioselective nitroaldol reaction of α-keto esters catalyzed by a copper(II)-bisoxazolidine complex

A wide range of aliphatic and aromatic -keto esters has been transformed to α-hydroxy-β-nitro esters via the Cu(II)-bisoxa-zolidine-catalyzed Henry reaction. In the presence of 10 mol% of the chiral catalyst, nitroaldol products were obtained in up to 95% yield and 76% ee.

Enantioselective addition of nitromethane to α-keto esters catalyzed by copper(II)-iminopyridine complexes

The copper complex of a chiral iminopyridine easily prepared from (R)-(-)-fenchone and picolylamine catalyzes the enantioselective Henry (nitroaldol) reaction between nitromethane and α-keto esters. Good yields and modest to good enantioselectivities are obtained for a wide range of α-keto esters, bearing aromatic, alkyl or alkenyl groups attached to the ketone carbonyl group. The Royal Society of Chemistry 2008.

Catalytic asymmetric nitroaldol (Henry) reaction with a zinc-fam catalyst

(Chemical Equation Presented) Ferrocenyl-substituted aziridinylmethanol (Fam-1) was used as a catalyst with zinc for the asymmetric nitroaldol (Henry) reaction. This catalyst worked with a variety of aldehydes (aromatic, aliphatic, α,β-unsaturated, and he

Enantioselective nitroaldol reaction of α-ketoesters catalyzed by cinchona alkaloids

The development of highly enantioselective and general catalytic nitroaldol (Henry) reactions with ketones is a challenging yet desirable task in organic synthesis. In this communication, we report an asymmetric nitroaldol reaction with α-ketoesters catalyzed by a new C6′-OH cinchona alkaloid catalyst. This is the first highly efficient organocatalytic asymmetric Henry reaction with ketones. This reaction is operationally simple and affords high enantioselectivity as well as good to excellent yield for a broad range of α-ketoesters. . Copyright

Copper-catalyzed enantioselective Henry reactions of α-keto esters: An easy entry to optically active β-nitro-α-hydroxy esters and β-amino-α-hydroxy esters

The catalytic enantioselective Henry reaction of α-keto esters with nitromethane has been developed. The reaction conditions have been optimized by the screening of different chiral Lewis acids, solvents, and bases, and it was found that the copper(II)-tert-butyl bisoxazoline complex in combination with triethylamine catalyzed a highly enantioselective reaction giving optically active β-nitro-α-hydroxy esters in high yields and with excellent enantiomeric excesses. The scope of the reaction is demonstrated by the reaction of a variety of different α-keto esters. The catalytic enantioselective Henry reaction of β,γ-unsaturated-α-keto esters proceeds as a 1,2-addition reaction exclusively, in contrast to the uncatalyzed reaction where both the 1,2- and 1,4-addition products are formed. It is demonstrated that the β-nitro-α-hydroxy esters can be converted into, e.g., Boc-protected β-amino-α-hydroxy esters in high yields and without loss of optical purity. The mechanism for the reaction is discussed, and it is postulated that both the α-keto ester and nitromethane/nitronate is coordinated to the metal center during the reaction course.