Category: 104322-63-6

Cermak, Diana M.; Du, Yanming; Wiemer, David F. published the artcile< Synthesis of Nonracemic Dimethyl α-(Hydroxyfarnesyl)phosphonates via Oxidation of Dimethyl Farnesylphosphonate with (Camphorsulfonyl)oxaziridines>, Category: isothiazole, the main research area is hydroxyfarnesylphosphonate preparation oxidation camphorsulfonyloxaziridine stereoselective.

Several strategies for synthesis of nonracemic di-Me α-(hydroxyfarnesyl)phosphonate and the parent phosphonic acid have been explored. Separation of diastereomeric derivatives prepared by esterification of racemic α-hydroxy phosphonate with (S)-(+)-O-methylmandelic acid was possible, and these diastereomers could be assigned absolute stereochem. on the basis of literature precedent. However, hydrolysis to the α-hydroxy phosphonic acid was accompanied by extensive isomerization. Addition of a nonracemic phosphonamidite to farnesal also gave nonracemic material, but again hydrolysis was problematic. Oxidation of di-Me farnesylphosphonate anion with nonracemic (camphorsulfonyl)oxaziridines was shown to be regio- and stereoselective for formation of the α-hydroxy phosphonate. Enantiomeric excess of ∼70% ee was established by conversion of the oxidation products to their (S)-(+)-O-methylmandelate derivatives Although hydrolysis of these Me esters was accompanied by extensive racemization, both enantiomers of α-(hydroxyfarnesyl)phosphonic acid were obtained in low ee by this strategy.

Journal of Organic Chemistry published new progress about Selective oxidation (regio- and stereoselective). 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Category: isothiazole.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Davis, Franklin A.; Wei, Jia; Sheppard, Aurelia C.; Gubernick, Steven published the artcile< The mechanism of hydroxylation of organometallic reagents by 2-sulfonyloxaziridines>, Computed Properties of 104322-63-6, the main research area is hydroxylation organometallic sulfonyloxaziridine mechanism; phenol octanol cresol.

The hydroxylation of organometallic reagents (e.g. PhMgBr) by 2-sulfonyloxaziridines (e.g. I) is shown to involve a hemiaminal intermediate, whose stability is apparently related to the nucleophilicity of the hydroxylated product (e.g. PhOH).

Tetrahedron Letters published new progress about Grignard reagents Role: RCT (Reactant), RACT (Reactant or Reagent). 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Computed Properties of 104322-63-6.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Page, Philip C. Bulman; Heer, Jag P.; Bethell, Donald; Collington, Eric W.; Andrews, David M. published the artcile< Asymmetric sulfide oxidation using [(3,3-dimethoxycamphoryl)sulfonyl]oxaziridine>, SDS of cas: 104322-63-6, the main research area is sulfoxide chiral; sulfide enantioselective oxidation dimethoxycamphorylsulfonyloxaziridine.

The system [(3,3-dimethoxycamphoryl)sulfonyl]oxaziridine/H2O2 oxidizes sulfides to sulfoxides cleanly and efficiently in up to 98% ee.

Tetrahedron: Asymmetry published new progress about Oxidation catalysts, stereoselective. 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, SDS of cas: 104322-63-6.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Cermak, Steven C.; Wiemer, David F. published the artcile< Synthesis of derivatives of (1R)-(-)- and (1S)-(+)-10-camphorsulfonic acid>, Recommanded Product: (4aS,7R,8aS)-9,9-Dimethyltetrahydro-4H-4a,7-methanobenzo[c][1,2]oxazireno[2,3-b]isothiazole 3,3-dioxide, the main research area is laboratory experiment enantiomer camphorsulfonic acid derivative preparation; camphorsulfonate oxaziridine enantiomer laboratory experiment preparation.

A new series of experiments for undergraduate organic chem. laboratory were developed at the University of Iowa, Iowa City, IA, to illustrate concepts of enantiomeric excess and the lack of correlation between absolute configuration and optical rotation. These experiments are based on the preparation of camphorsulfonyloxaziridine derivatives

Journal of Chemical Education published new progress about Absolute configuration. 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Recommanded Product: (4aS,7R,8aS)-9,9-Dimethyltetrahydro-4H-4a,7-methanobenzo[c][1,2]oxazireno[2,3-b]isothiazole 3,3-dioxide.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Glahsl, Gudrun; Herrmann, Rudolf published the artcile< (+)-(3-Oxocamphorsulfonyl)oxaziridine as a highly stereoselective reagent for the oxidation of sulfides to chiral sulfoxides>, HPLC of Formula: 104322-63-6, the main research area is stereoselective oxidation sulfide oxocamphorsulfonyloxaziridine; sulfoxide chiral asym synthesis; aldehyde sulfinyl chiral.

The synthesis of the title oxaziridine (I) and its application to the enantio- or diastereoselective oxidation of sulfides to sulfoxides is described. Enantiomeric excesses up to 66% are observed, showing the reagent to be superior to most other oxidizing systems. The exceedingly mild reaction conditions (aprotic, neutral) allow the preparation of several chiral α-sulfinyl aldehydes. The properties. of these compounds are discussed.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) published new progress about Stereochemistry. 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, HPLC of Formula: 104322-63-6.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Hynninen, Paavo H.; Leppaekases, Tuomo S.; Mesilaakso, Markku published the artcile< The enolate anions of chlorophylls a and b as ambident nucleophiles in oxidations with (-)- or (+)-(10-camphorsulfonyl)oxaziridine. Synthesis of 132(S/R)-hydroxychlorophylls a and b>, Application In Synthesis of 104322-63-6, the main research area is chlorophyll enolate stereoselective hydroxylation camphorsulfonyloxaziridine mechanism; ambident nucleophile chlorophyll enolate; hydroxychlorophyll diastereoselective preparation carbon NMR.

The enolate anions of chlorophylls (Chl) are ambident nucleophiles that are of considerable organic chem. interest in relation to the theory of electron delocalization (aromaticity) and charge-transfer in large conjugated π-systems, as well as for their chem. reactivity. Under deaerated conditions, the (-)- and (+)-enantiomers of (10-camphorsulfonyl)oxaziridine (CSOAI) are effective oxidants for the enolate anions of Chl a and Chl b, when 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) serves as a base. The use of these sterically hindered reagents to hydroxylate Chl a and Chl b is described for the first time. The total yield of 132(S/R)-HO-Chl a was 71 and 90% for the oxidations of Chl a with (-)-CSOAI and (+)-CSOAI, resp. Chl b, however, behaved clearly differently from Chl a. The total yield of 132(S/R)-HO-Chl b was 40% in the oxidation with (-)-CSOAI and 60% in the reaction with (+)-CSOAI. A competing side-reaction, which resulted in the 152-Me, 173-phytyl ester of Mg-151(S/R)-unstable rhodin, was found to lower the yields of the desired main products. The formation of the side-products was largely avoided and the yield of 132(S/R)-HO-Chl b was improved by increasing the volume of hexane and using phosphate buffer in the first step of the work-up. With (-)-CSOAI, a 94% diastereomeric excess (de) was achieved for 132(R)-HO-Chl a, whereas the de for 132(R)-HO-Chl b was 66%. With (+)-CSOAI, the de was 10% for 132(R)-HO-Chl a and 8% for 132(R)-HO-Chl b. The results were interpreted in terms of a nucleophilic reaction mechanism, kinetically controlled by steric hindrance, originating on the one hand in the 17-propionate phytyl ester side-chain, protruding over the isocyclic ring E of the Chl enolate ion, and however, in the bulky camphorsulfonyl unit of CSOAI. Possible reasons for the different results from the Chl b oxidations as compared with those of the Chl a oxidations are discussed. Comparison of the differences in the NMR δC-values between 132(S)- and 132(R)-HO-Chl a as well as those between 132(S)- and 132(R)-HO-Chl b, indicated that the change of stereochem. configuration at C-132 induces only slight differences in the δC-values. Of special interest are the δC-values of C-132, which are at ∼91 ppm for the a- and b-series diastereomers. This C is deshielded by ∼25 ppm relative to the C-132 of 132(R)-Chl a (δC = 65.5). Owing to this, 13C NMR spectroscopy is a good method to distinguish the 132-hydroxylated chlorophylls from the intact, naturally occurring chlorophylls.

Tetrahedron published new progress about Hydroxylation, stereoselective. 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Application In Synthesis of 104322-63-6.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Davis, Franklin A.; Reddy, R. Thimma; Reddy, Rajarathnam E. published the artcile< Asymmetric synthesis of sulfinimines: applications to the synthesis of nonracemic β-amino acids and α-hydroxyl β-amino acids>, Computed Properties of 104322-63-6, the main research area is asym synthesis sulfinimine; beta amino acid; hydroxy beta amino acid; stereoselective oxidation sulfenimine dichlorocamphoryloxaziridine; chlorocamphoryloxaziridine stereoselective oxidation sulfenimine; camphoryloxaziridine dichloro stereoselective oxidation sulfenimine; oxaziridine dichlorocamphoryl stereoselective oxidation sulfenimine.

Asym. oxidation of sulfenimines I (Ar = Ph, R = H, X = H, MeO; Ar = p-tolyl, R = Me, X = H) with chiral oxaziridines II or III affords sulfinimines IV or V (88-90% ee), which are chiral ammonia imine synthons useful in the enantioselective synthesis of β-amino acids and α-hydroxy β-amino acids such as the C-13 side chain of taxol.

Journal of Organic Chemistry published new progress about Amino acids, hydroxy Role: SPN (Synthetic Preparation), PREP (Preparation). 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Computed Properties of 104322-63-6.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Davis, Franklin A.; Haque, M. Serajul; Ulatowski, Terrance G.; Towson, James C. published the artcile< Asymmetric oxidation of ester and amide enolates using new (camphorylsulfonyl)oxaziridines>, Formula: C10H15NO3S, the main research area is asym oxidation amide ester enolate; camphorylsulfonyloxaziridine asym oxidation; oxaziridine camphorylsulfonyl asym oxidation.

The first asym. oxidation of ester and amide lithium enolates RR1CHCOR2 (R = H, Me; R1 = Ph, PhCH2; R2 = MeO, Me3CO, pyrrolidino) to optically active α-hydroxy carbonyl compounds RR1C(OH)COR2 is reported using new, easily prepared, stable (camphorylsulfonyl)oxaziridines (+)-(2R,8aS)-I and (-)-(2S,8aR)-II. Either enantiomer of RR1C(OH)COR2 can be readily obtained because the configuration of the oxaziridine three-membered ring determines the product stereochem.

Journal of Organic Chemistry published new progress about Enols, esters Role: RCT (Reactant), RACT (Reactant or Reagent). 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Formula: C10H15NO3S.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Mahale, Rajendra D.; Rajput, Mahesh R.; Maikap, Golak C.; Gurjar, Mukund K. published the artcile< Davis Oxaziridine-Mediated Asymmetric Synthesis of Proton Pump Inhibitors Using DBU Salt of Prochiral Sulfide>, Quality Control of 104322-63-6, the main research area is camphorsulfonyl oxaziridine asym sulfoxidation sulfide omeprazole PPI preparation.

A simple and clean asym. synthesis of proton pump inhibitors using inexpensive 10-camphorsulfonyl oxaziridine is described. The activation of prochiral sulfide is based on use of the DBU salt which is capable of enhancing the reactivity and enantioselectivity.

Organic Process Research & Development published new progress about Enantioselective synthesis. 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Quality Control of 104322-63-6.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Pogatchnik, Diana M.; Wiemer, David F. published the artcile< Enantioselective synthesis of α-hydroxy phosphonates via oxidation with (camphorsulfonyl)oxaziridines>, SDS of cas: 104322-63-6, the main research area is phosphonate hydroxy enantioselective preparation; hydroxylation enantioselective phosphonate oxaziridine camphorsulfonyl; chiral phosphonate hydroxy preparation.

Reaction of phosphonate anions with enantiomerically pure (camphorsulfonyl)oxaziridines gave nonracemic α-hydroxy phosphonates. This enantioselective hydroxylation methodol. provides convenient access to optically active α-hydroxy phosphonates and their corresponding phosphonic acids. E.g., treating PhCH2P(O)(OMe)2 with (Me3Si)2NNa in THF gave 70% (S)-PhCH(OH)P(O)(OMe)2 (93% ee).

Tetrahedron Letters published new progress about Hydroxylation, stereoselective. 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, SDS of cas: 104322-63-6.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com