109853-54-5

Upstream product

• 102-92-1 cinnamoyl chloride 
• 109853-51-2 N-tributylstannyl-2-oxazolidinone 
• 497-25-6 dimethylenecyclourethane 
• 621-82-9 Cinnamic acid 
• 104-54-1 3-Phenylpropenol 

Downstream Products

• 186642-46-6 3-(benzyloxyamino)-3-(3-phenylpropanoyl)oxazolidin-2-one 
• 1309230-97-4 C₂₃H₂₄N₂O₃ 
• 1334952-09-8 (R)-3-[3-(cyclopentylthio)-3-phenylpropanoyl]oxazolidin-2-one 
• 1334952-08-7 (R)-3-[3-(furan-2-ylmethylthio)-3-phenylpropanoyl]oxazolidin-2-one 
• 1334952-04-3 (R)-3-[3-(benzylthio)-3-phenylpropanoyl]oxazolidin-2-one 
• 1334952-18-9 (-)-(S)-3-(3-(benzylthio)-3-phenylpropanoyl)oxazolidin-2-one 
• 1349194-94-0 3-((1S,2S)-4-methylene-2-phenylcyclopentanecarbonyl)oxazolidin-2-one 
• 1374559-30-4 C₂₆H₂₆NO₆P 
• 1244964-95-1 C₂₄H₂₂NO₄P 

Relevant academic research and scientific papers

Stereocontrolled Synthesis of trans/ cis-2,3-Disubstituted Cyclopropane-1,1-diesters and Applications in the Syntheses of Furanolignans

A new Michael addition/intramolecular alkylation sequence of (Z)-3-(2-bromo-3-arylacryloyl)oxazolidin-2-ones and malonates was developed. By a simple switch of the reaction conditions including the base promoter, solvent, and reaction temperature, both of the cis- and trans-isomers of a series of oxazolidinone-containing 2,3-disubstituted cyclopropane-1,1-diesters could be obtained in good-to-excellent yields and with an excellent diastereoselectivity. The utility of the cyclopropane products was demonstrated in the diastereoselective syntheses of (±)-urinaligran and a stereoisomer of (±)-virgatusin involving the AlCl3-promoted [3+2] annulation with veraldehyde or piperonal as the key step.

CuCl/TMEDA/nor-AZADO-catalyzed aerobic oxidative acylation of amides with alcohols to produce imides

Although aerobic oxidative acylation of amides with alcohols would be a good complement to classical synthetic methods for imides (e.g., acylation of amides with activated forms of carboxylic acids), to date, there have been no reports on oxidative acylation to produce imides. In this study, we successfully developed, for the first time, an efficient method for the synthesis of imides through aerobic oxidative acylation of amides with alcohols by employing a CuCl/TMEDA/nor-AZADO catalyst system (TMEDA = teramethylethylendiamine; nor-AZADO = 9-azanoradamantane N-oxyl). The proposed acylation proceeds through the following sequential reactions: aerobic oxidation of alcohols to aldehydes, nucleophilic addition of amides to the aldehydes to form hemiamidal intermediates, and aerobic oxidation of the hemiamidal intermediates to give the corresponding imides. This catalytic system utilizes O2 as the terminal oxidant and produces water as the sole by-product. An important point for realizing this efficient acylation system is the utilization of a TMEDA ligand, which, to the best of our knowledge, has not been employed in previously reported Cu/ligand/N-oxyl systems. Based on experimental evidence, we consider that plausible roles of TMEDA involve the promotion of both hemiamidal oxidation and regeneration of an active CuII-OH species from a CuI species. Here promotion of hemiamidal oxidation is particularly important. Employing the proposed system, various types of structurally diverse imides could be synthesized from various combinations of alcohols and amides, and gram-scale acylation was also successful. In addition, the proposed system was further applicable to the synthesis of α-ketocarbonyl compounds (i.e., α-ketoimides, α-ketoamides, and α-ketoesters) from 1,2-diols and nucleophiles (i.e., amides, amines, and alcohols).

SYNTHESIS OF FUNCTIONALIZED AND UNFUNCTIONALIZED OLEFINS VIA CROSS AND RING-CLOSING METATHESIS

The invention is directed to the cross-metathesis and ring-closing metathesis reactions between geminal disubstituted olefins and terminal olefins, wherein the reaction employs a Ruthenium or Osmium metal carbene complex. Specifically, the invention relates to the synthesis of alpha-functionalized or unfunctionalized olefins via intermolecular cross-metathesis and intramolecular ring-closing metathesis using a ruthenium alkylidene complex. The catalysts preferably used in the invention are of the general formulawherein:M is ruthenium or osmium;X and Xare each independently an anionic ligand;L is a neutral electron donor ligand; and,R, RR, R, R, and Rare each independently hydrogen or a substituent selected from the group consisting of C1-C20 alkyl, C2-C20 alkenyl, C2-C20 alkynyl, aryl, C1-C20 carboxylate, C1-C20 alkoxy, C2-C20 alkenyloxy, C2-C20 alkynyloxy, aryloxy, C2-C20 alkoxycarbonyl, C1-C20 alkylthio, C1-C20 alkylsulfonyl and C1-C20 alkylsulfinyl.

Cinchona Alkaloid Catalyzed Sulfa-Michael Addition Reactions Leading to Enantiopure β-Functionalized Cysteines

Sulfa-Michael additions to α,β-unsaturated N-acylated oxazolidin-2-ones and related α,β-unsaturated α-amino acid derivatives have been enantioselectively catalyzed by Cinchona alkaloids functionalized with a hydrogen bond donating group at the C6′ position. The series of Cinchona alkaloids includes known C6′ (thio)urea and sulfonamide derivatives and several novel species with a benzimidazole, squaramide or a benzamide group at the C6′ position. The sulfonamides were especially suited as bifunctional organocatalysts as they gave the products in very good diastereoselectivity and high enantioselectivity. In particular, the C6′ sulfonamides catalyzed the reaction with the α,β-unsaturated α-amino acid derivatives to afford the products in a diastereomeric ratio as good as 93:7, with the major isomer being formed in an ee of up to 99%. The products of the organocatalytic sulfa-Michael addition to α,β-unsaturated α-amino acid derivatives were subsequently converted in high yields to enantiopure β-functionalized cysteines suitable for native chemical ligation.

O-trifluoromethylation of N,N-disubstituted hydroxylamines with hypervalent iodine reagents

A mild trifluoromethylation reaction of N,N-disubstituted hydroxylamines that is tolerant towards a variety of functional groups, including nitriles, alcohols, ketones, esters, amides, imides, and nitrogen heterocycles, is reported. The key feature of this reaction is the activation of the CF 3 reagent with either trimethylsilyl triflate or LiClO4 and partial or full deprotonation of the substrate with tetramethylguanidine or lithium diisopropylamide. Products were obtained in up to 80 % yield. Preliminary mechanistic studies suggested that the reaction follows a radical pathway in which the deprotonated hydroxylamine and a Lewis or Bronsted acid activated CF3 reagent engages in a single-electron-transfer step to generate a pair of radicals that recombine to afford the desired product. The trifluoromethylation procedure was successfully used in the modification of secondary nitrogen groups of pharmaceutically relevant targets (Fluoxetine and Mefloquine), which afforded new derivatives containing a novel N-trifluoromethoxy moiety. Copyright

Asymmetric β-boration of α,β-unsaturated N -acyloxazolidinones by [2.2]paracyclophane-based bifunctional catalyst

An efficient copper-catalyzed asymmetric conjugate boration has been achieved by exploiting a new planar and central chiral bicyclic triazolium ligand. This protocol was highly efficient and gave a variety of chiral secondary alkylboronates in 97-99% ee. A preliminary mechanistic study supports the bifunctional nature of the catalyst.

DCC/DMAP-Mediated Coupling of Carboxylic Acids with Oxazolidinones and Thiazolidinethiones

Dicyclohexylcarbodiimide and catalytic dimethylaminopyridine were successfully used in the coupling of carboxylic acids with oxazolidinones and thiazolidinethiones. The acylated products were obtained in good yields.

Formation of N-Tributylstannyl-2-oxazolidone from (Bu3Sn)2O and 2-Chloroethyl Isocyanate

N-Tributylstannyl-2-oxazolidone is formed from the reaction of (Bu3Sn)2O and 2-chloroethyl isocyanate in the presence of hexamethylphosphoric triamide, and reacts with electrophiles to give N-substituted 2-oxazolidones in good yields.