125572-22-7

Upstream product

• 5856-63-3 (2R)-2-aminobutan-1-ol 
• 98-59-9 p-toluenesulfonyl chloride 
• 137845-37-5 4-methyl-N-((1E,2E)-3-phenylallylidene)benzenesulfonamide 
• 40916-56-1 (R)-2-Amino-butan-1-ol; hydrochloride 
• 124-38-9 carbon dioxide 
• 159518-55-5 (3S)-Methyl-N-p-toluolsulfonylaziridin-(2R)-carbonsaeuremethylester 
• 43188-56-3 methyl (2R,3R)-3-hydroxy-2-(4-methylphenyl)sulfonamidobutanoate 

Downstream Products

• 139192-58-8 (S)-2-[(2R,4R)-4-Ethyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-cyclopentanone 
• 139192-67-9 (R)-2-[(2R,4R)-4-Ethyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-cyclopentanone 
• 139192-52-2 (S)-2-[(2R,4R)-4-Ethyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-cyclohexanone 
• 139192-61-3 (R)-2-[(2R,4R)-4-Ethyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-cyclohexanone 
• 334686-43-0 (-)-(2S,4R)-4-ethyl-2-ethyloxy-3-[(4-methylphenyl)sulfonyl]-1,3-oxazolidine 
• 898558-09-3 2,2'-diacetoxy-5,5'-di-tert-butyl-3,3'-bis[(2R,4R)-4-ethyl-3-(4-methylbenzenesulfonyl)-1,3-oxazolidinyl]biphenyl 
• 1268630-68-7 C₁₅H₂₁NO₃S 
• 1268630-59-6 C₁₅H₂₃NO₄S 
• 1268631-01-1 C₂₅H₃₉NO₆S 

Relevant academic research and scientific papers

Diastereoselective formation of 2-aryl-3-arenesulfonyl 4-ethyl-1,3-oxazolidines: An X-ray crystallographic and 1H NMR study

N-Arylsulfonamides of (R)- and (S)-2-amino-1-butanol, on condensation with aromatic aldehydes produced diastereomerically pure 2-aryl-3-arenesulfonyl 4-ethyl-1,3-oxazolidines. The absolute configurations of one enantiomeric pair have been determined from

Chiral NHC Ligands Bearing a Pyridine Moiety in Copper-Catalyzed 1,2-Addition of Dialkylzinc Reagents to β-Aryl-α,β-unsaturated N-Tosylaldimines

Asymmetric 1,2-addition of dialkylzinc reagents to α,β-unsaturated N-tosylaldimines was catalyzed by copper salt in the presence of chiral imidazolium salts having a pyridine ring, which were derived from amino acid, to afford the corresponding chiral allylic amines with up to 91% ee in reasonably high yields. The chiral N-heterocyclic carbene (NHC) ligand played an important role in controlling chemoselectivity.

Reagent-switch controlled metal-free intermolecular geminal diamination and aminooxygenation of vinylarenes

We report here the first general method for the geminal diamination and an intermolecular metal-free, geminal aminooxygenation of vinylarenes using hypervalent iodine reagent. A new m-CPBA mediated geminal aminooxygenation is also reported. A novel reagent-switch for the control of migrating group by controlling the two independent geminal addition paths is developed. Deuterium labelling studies and the control studies have provided unambiguous evidences for the phenyl migration and hydride migration in the oxidative geminal difunctionalization process mediated by PhI(OCOCF3)2and m-CPBA, respectively through a semi-pinacol rearrangement.

Stereo- and regioselective synthesis of polysubstituted chiral 1,4-oxazepanes

The number of cyclic molecular scaffolds available to medicinal chemists remains limited, and simple structures such as oxazepanes are still made using multistep procedures, including a number of protection/deprotection steps and purifications. We report

Gold-catalyzed direct activation of allylic alcohols in the stereoselective synthesis of functionalized 2-vinyl-morpholines

Alcohol versus alcohol: A highly stereocontrolled synthesis of substituted morpholines is realized by means of gold-catalyzed dehydrative allylic cyclization of diols (see scheme for one example; segphos = 5,5′-bis[di(3, 5-di-tert-butyl-4-methyoxyphenyl)phosphine]-4,4′-bi-1,3-benzodioxole). The present methodology represents one of the few examples of enantioselective gold-catalyzed transformations involving unactivated alkenes. Copyright

Synthesis of chiral oxazolidin-2-ones by 1,2-amino alcohols, carbon dioxide and electrogenerated acetonitrile anion

An improved electrochemical synthesis of chiral oxazolidin-2-ones from chiral 1,2-amino alcohols is obtained by direct electrolysis of solutions of MeCN-TEAP containing the amino alcohol, with subsequent CO2 bubbling and addition of TsCl. This

First enantioselective total synthesis of both (+)- and (-)-metachromin A

The antineoplastic agent (-)-metachromin A (1) from Hippospongia metachromia has been synthesized in enantiomerically pure form in 13% overall yield. A general convergent synthetic strategy for different metachromins using a 2-alkyloxy-3-sulfonyl-l,3-oxazolidine as a chiral dithienium equivalent is presented.

New isoxazolidine-based chiral auxiliaries for asymmetric syntheses

New chiral auxiliaries based on the bicyclic-isoxazolidine skeleton, 3-oxa-2,7-diazabicylo[3,3,0]octane derivatives, were synthesized in 60-80% overall yields from amino acids. Asymmetric alkylation and boron aldol reaction using the auxiliaries proceeded with high selectivities. 'Carboxylic amide' has been used for the asymmetric boron-mediated aldol reaction for the first time.

Synthesis of optically pure 2-Aziridinemethanols: Versatile synthetic building blocks

Synthesis of three cis-trans pairs of N-sulfonylated-2-aziridinemethanols starting from (S)-threonine, (R)-allothreonine, a chiral 2-amino alcohol, or enantiomerically enriched 2,3-epoxy alcohols is described. A synthetic route to N-tosyl- and N-mesyl-2-a

Diastereoselective synthesis of enantiomerically pure 3-organosulfonyl-2-(2-oxocycloalkyl)-1,3-oxazolidines from 2-formylcycloalkanones and β-aminoalkanols

The title compounds (3-arylsulfonyl- or 3-mesyl-2-(2-oxocycloalkyl)-1,3-oxazolidines) belonging to two different diastereomeric series, are prepared selectively by variation of the condensation conditions. By this, the chiral information of the 2-amino-1-