61444-22-2

Upstream product

• 102-01-2 N-phenylacetoacetamide 
• 127604-19-7 (S)-3-tert-butyldimethylsilyloxybutananilide 
• 62-53-3 aniline 
• 1954-91-2 3-hydroxy-N-phenylbutansaeureamid 
• 98-88-4 benzoyl chloride 
• 103-71-9 phenyl isocyanate 
• 75-07-0 acetaldehyde 
• 31729-70-1 bis(iodozinc)methane 
• 17645-30-6 (E)-crotonanilide 

Downstream Products

• 127643-62-3 (R)-4-methyl-N-phenylazetidine-2-one 
• 127604-11-9 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (R)-1-methyl-2-phenylcarbamoyl-ethyl ester 
• 127604-10-8 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-1-methyl-2-phenylcarbamoyl-ethyl ester 
• 127604-20-0 (S)-3-mesyloxybutanylide 

Relevant academic research and scientific papers

Preparation of the zinc enolate equivalent of amides by zinciomethylation of isocyanates: Catalytic asymmetric Reformatsky-type reaction

Bis(iodozincio)methane [CH2(ZnI)2] transforms isocyanates (R-N=C=O) into the enolate equivalent of amides via zinciomethylation. The reactivity of the enolate equivalent as a nucleophile toward aldehydes depends on the R group of the

Catalytic asymmetric aldol-type reaction of zinc enolate equivalent of amides

Treatment of phenyl isocyanate with bis(iodozincio)methane gave a zinciomethylenated product, which acts as an amide-enoate equivalent. It did not react with an aldehyde efficiently, but gave the corresponding adduct in good yield in the presence of an aminoalcohol. Use of a catalytic amount of chiral aminoalcohol led the process to the catalytic asymmetric Aldol-type reaction.

Synthesis and Suzuki-Miyaura cross-coupling of enantioenriched secondary potassium β-trifluoroboratoamides: Catalytic, asymmetric conjugate addition of bisboronic acid and tetrakis(dimethylamino)diboron to α,β- unsaturated carbonyl compounds

Enantioenriched potassium β-trifluoroboratoamides have been synthesized via an asymmetric, copper-catalyzed 1,4-addition of tetrahydroxydiboron (BBA) and tetrakis(dimethylamino)-diboron to α,β-Unsaturated amides. These dibora reagents provide access to the desired organotri-fluoroborates using effective and atom economical sources of boron. The copper-catalyzed β-boration is extended to α,β- Unsaturated ketones and esters. The desired potassium organotrifluoroborates are synthesized with yields up to 92% and enantiomeric ratios up to 98:2. The enantioenriched potassium btrifluoroboratoamides are successfully cross-coupled with an array of aryl and heteroaryl chlorides in high yield with complete stereochemical fidelity as the transmetalation proceeds through an SE2 mechanism via an open transition state.

Ru-catalyzed asymmetric hydrogenation of 3-oxoglutaric acid derivatives via solvent-assisted pinpoint recognition of carbonyls in close chemical propinquity

Upon comparison of hydrogenation rates of various β-ketocarboxylic acid derivatives, β-ketoamides were found to be hydrogenated slightly faster than β-ketoesters in EtOH in the presence of [RuCl(benzene)(S)- SunPhos]Cl at 70 °C with 20 bar of hydrogen. In THF these differences were so sharpened that β-ketoamides were hydrogenated even faster than in EtOH while the esters were extremely slow. Based on these findings, a series of 3-oxoglutaric acid derived with ester and amide moieties on the two ends were hydrogenated to 3-hydroxyl products with high enantioselectivities.

Nonenzymatic kinetic resolution of 3-hydroxyalkanamides with chiral copper catalyst

Kinetic resolution of 3-hydroxyalkanamides with good to high selectivities was achieved by benzoylation using copper(II) triflate and (R,R)-PhBox [2,2′-isopropylidenebis(4-phenyl-2-oxazoline)] as catalyst, which also mediated enantioselective tosylation o

Ru-SYNPHOS and Ru-DIFLUORPHOS: Highly efficient catalysts for practical preparation of β-hydroxy amides

Ru-SYNPHOS and Ru-DIFLUORPHOS catalysts were efficiently used for the synthesis of a wide variety of chiral β-hydroxy amides via asymmetric hydrogenation of the corresponding β-keto amides. Georg Thieme Verlag Stuttgart.

Asymmetric Reduction of Functionalized Ketones with a Sodium Borohydride-(L)-Tartaric Acid System

The sodium borohydride-(L)-tartaric acid system is effective for the asymmetric reduction of prochiral ketones if they are functionalized on the α- or β-carbon with a group that can chelate to the chirally modified borohydride.

Yeast-Mediated Reduction of N-Substituted Acetoacetamides. Improvement of Conversion by Immobilization

N-Ethylacetoacetamide and acetoacetanilide were enantioselectively converted into the corresponding (S)-3-hydroxy compounds by alginate- or polyurethane-immobilized baker's yeasts, while whithout immobilization the yield of the yeast-mediated reaction was very low.