Category: 104322-63-6

Davis, Franklin A.; Weismiller, Michael C. published the artcile< Enantioselective synthesis of tertiary α-hydroxy carbonyl compounds using [(8,8-dichlorocamphoryl)sulfonyl]oxaziridine>, Formula: C10H15NO3S, the main research area is carbonyl compound alpha hydroxy asym synthesis; chlorocamphorylsulfonyloxaziridine oxidizing agent; tetralone enolate oxidation asym oxaziridine.

Very high stereoinduction, generally 90-95% ee, is observed for the asym. oxidation of 2-substituted-1-tetralone enolates to 2-hydroxy-2-substituted-1-tetralones by (+)-(8,8-dichlorocamphorylsulfonyl)oxaziridine (I), a new oxaziridine type. Not only are these tertiary-α-hydroxy carbonyl compounds difficult to prepare, enantiomerically pure, via other methods, but they are also models for several biol. active compounds This new asym. oxidizing reagent also affords exceptional ee’s for the asym. oxidation of acyclic ketone enolates as well. For example, oxidation of the sodium enolate of 1-phenylpropanone with I affords (S)-2-hydroxy-1-phenylpropanone in greater than 95% ee. I is prepared in two steps, in good overall yield, from (camphorsulfonyl)imine II. The results of this study demonstrate that modification of the oxaziridine active site is an efficient method for improving enolate oxidation stereoselectivities.

Journal of Organic Chemistry published new progress about Oxidation, stereoselective. 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Formula: C10H15NO3S.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Davis, Franklin A.; Reddy, G. Venkat; Chen, Bang-Chi; Kumar, Anil; Haque, M. Serajul published the artcile< Enantioselective Synthesis of 2-Methyl-2-hydroxy-γ-butyrolactone and Its Application in the Asymmetric Synthesis of Frontalin and Mevalonolactone>, COA of Formula: C10H15NO3S, the main research area is asym hydroxylation methylbutyrolactone phenylisobutyrate; camphorsulfonyloxaziridine chiral auxiliary hydroxylation; frontalin formal asym synthesis; mevalonolactone asym synthesis.

The asym. hydroxylation of the enolates of (R)-menthyl 2-methyl-3-phenylpropionate (I) and 2-methyl-γ-butyrolactone (II) with (camphorylsulfonyl)oxaziridines was studied. The stereoselectivities of the tertiary α-hydroxy carbonyl products were highly dependent on the enolate structure, the oxidizing reagents, and the reaction conditions. While high diastereoselectivity (up to 94%) was obtained for enolates of I with substoichiometric amounts of (camphorylsulfonyl)oxaziridine, the yields were unsatisfactory. On the other hand, the enantioselective α-hydroxylation of the sodium enolate of II with [(8,8-dimethoxycamphoryl)sulfonyl]oxaziridine afforded α-hydroxy lactone in 70% yield and 84% ee. The enantiomeric excess was improved to >93% ee by crystallization of the corresponding benzoate. The utility of both enantiomers of the benzoate was demonstrated in the formal asym. synthesis of (1S,5R)-(-)-frontalin and in the asym. synthesis of (R)-(-)-mevalonolactone.

Journal of Organic Chemistry published new progress about Chiral synthons. 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, COA of Formula: C10H15NO3S.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Polywka, Mario E. C. published the artcile< Camphor based auxiliaries for asymmetric synthesis>, Category: isothiazole, the main research area is camphor chiral auxiliary asym synthesis review; bornanesultam chiral auxiliary review; oxaziridine camphorsulfonyl chiral auxiliary review.

A review of chiral auxiliaries, e.g. bornane-10,2-sultams, N-acylsultams, and (camphorsulfonyl)oxaziridines in asym. synthesis of amino acids, aldol condensations, and asym. alkylations with 14 references

Chimica Oggi published new progress about Chiral synthons. 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Category: isothiazole.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Bunnage, Mark E.; Burke, Anthony J.; Davies, Stephen G.; Goodwin, Christopher J. published the artcile< Asymmetric synthesis of (2S,3R)-3-amino-2-hydroxydecanoic acid: the unknown amino acid component of microginin>, Application In Synthesis of 104322-63-6, the main research area is asym synthesis aminohydroxydecanoic acid; absolute configuration microginin aminohydroxydecanoic acid.

3-Amino-2-hydroxydecanoic acid (AHDA) is an unusual amino acid purported to occur in the recently isolated angiotensin-converting enzyme inhibitor microginin. In order to elucidate the stereochem. of the naturally occurring material, and thus complete the structural assignment of microginin, both the (2R,3R)-anti-diastereoisomer and the (2S,3R)-syn-diastereoisomer of AHDA have been prepared Comparison of the 1H and 13C NMR spectroscopic data of the synthetic amino acids with that reported for the naturally occurring material indicates that the relative stereochem. of the AHDA found in microginin is syn. The absolute stereochem. of the natural amino acid is shown to be (2S,3R) by comparison of its reported CD spectrum with that recorded for the synthetic material prepared herein.

Tetrahedron: Asymmetry published new progress about Absolute configuration. 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

Josien, Hubert; Curran, Dennis P. published the artcile< Synthesis of (S)-mappicine and mappicine ketone via radical cascade reaction of isonitriles>, Safety of (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 mappicine synthesis; radical cascade isonitrile.

(S)-mappicine (I) and mappicine ketone were prepared from Me acetoacetate by a strategy featuring a radical cascade reaction of II with Ph isonitrile as the key step. The introduction of the hydroxy group of (S)-mappicine occurred with moderate selectivity through asym. hydroxylation.

Tetrahedron published new progress about Radical cyclization. 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Safety of (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

Fujiwara, Kenshu; Goto, Akiyoshi; Sato, Daisuke; Kawai, Hidetoshi; Suzuki, Takanori published the artcile< Stereoselective synthesis of cis- and trans-2,3-disubstituted eight-membered medium-ring ethers based on Ireland-Claisen rearrangement of 3-alkoxy-2-propenyl glycolate esters and ring-closing olefin metathesis>, Reference of 104322-63-6, the main research area is alkoxy propenyl glycolate ester preparation Ireland Claisen rearrangement; ether preparation ring closing olefin metathesis; disubstituted eight membered medium ring ether stereoselective preparation.

A simple stereoselective synthesis of cis- and trans-2,3-disubstituted medium-sized cyclic ethers was developed based on geometry-selective synthesis of 3-alkoxy-2-propenyl glycolate esters, Ireland-Claisen rearrangement of the glycolate esters, and ring-closing olefin metathesis.

Tetrahedron Letters published new progress about Cyclization (olefin metathesis). 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Reference of 104322-63-6.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Escalante, Jaime; Juaristi, Eusebio published the artcile< Enantioselective synthesis of β-amino acids. 6. High 1,2-stereoinduction in the preparation of enantiopure 2(R)-hydroxy-3(R)-N-benzoylamino-3-phenylpropionic acid (like stereoisomer of Taxol's side chain)>, Formula: C10H15NO3S, the main research area is stereoselective hydroxylation phenylperhydropyrimidinone camphor oxaziridine; pyrimidinone phenylperhydro stereoselective hydroxylation oxaziridine; asym synthesis phenylisoserine.

The remarkably high 1,2-stereoinduction encountered in the hydroxylation of 6(S)-phenylperhydropyrimidin-4-one I allows for the preparation of enantiopure N-benzoyl (2R,3R)-3-phenylisoserine (II), the like stereoisomer of taxol’s C-13 side chain.

Tetrahedron Letters 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, Formula: C10H15NO3S.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Towson, James C.; Weismiller, Michael C.; Lal, G. Sankar; Sheppard, Aurelia C.; Kumar, Anil; Davis, Franklin A. published the artcile< Synthesis of (+)-(2R,8aS)-10-(camphorylsulfonyl)oxaziridine>, Reference of 104322-63-6, the main research area is camphorylsulfonyloxaziridine; oxaziridine camphorylsulfonyl.

Amidation of (+)-10-camphosulfonyl chloride by NH4OH in CH2Cl2 gave 90% (+)-(1S)-1-camphorsulfonamide which underwent Amberlyst 15 catalyzed cyclocondensation in PhMe to give 90-95% imine I. The last was treated with aqueous oxone and K2CO3 to give 84% title compound II.

Organic Syntheses published new progress about 104322-63-6. 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Reference of 104322-63-6.

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

McClure, Cynthia K.; Grote, Christopher W. published the artcile< α,β-Functionalization of enones via pentacovalent oxaphospholenes>, Safety of (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 oxaphospholene functionalization enone; phosphonate keto acylvinyl.

2,2,2-Triethoxy-1,2λ5-oxaphospholene reacts under mild, neutral conditions with bromine, dialkyl azodicarboxylates, and oxaziridines to produce β-heteroatom substituted γ-ketophosphonates and β-acyl vinyl phosphonate in high yields.

Tetrahedron Letters published new progress about 104322-63-6. 104322-63-6 belongs to class isothiazole, and the molecular formula is C10H15NO3S, Safety of (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

Bunnage, Mark E.; Davies, Stephen G.; Goodwin, Christopher J. published the artcile< Asymmetric synthesis of allophenylnorstatine>, Computed Properties of 104322-63-6, the main research area is asym synthesis allophenylnorstatine; norstatine allophenyl asym synthesis.

The title compound (I), a component of the HIV-1 protease inhibitor kynostatin, has been prepared via a tandem conjugate addition-electrophilic hydroxylation strategy using lithium (S)-(α-methylbenzyl)benzylamide and (+)-(camphorsulfonyl)oxaziridine. The effects of mol. recognition and enolate geometry on the selectivity of the reaction are discussed.

Synlett published new progress about Stereoselective synthesis. 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