61444-22-2

Upstream product

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

Downstream Products

• 127604-20-0 (S)-3-mesyloxybutanylide 
• 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 

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

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.

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.

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.