| Identification | More | [Name]
(1S)-(+)-(Camphorylsulfonyl)oxaziridine | [CAS]
104322-63-6 | [Synonyms]
(1S)-(+)-(10-CAMPHORSULFONYL)OXAZIRIDINE
(1S)-(+)-(10-CAMPHORSULPHONYL)OXAZIRIDINE
(1S)-(+)-2,N-EPOXY-EXO-10,2-BORNANESULTAM
(1S)-(+)-(CAMPHORYLSULFONYL)OXAZIRIDINE
(+)-(2R,8AS)-(CAMPHORYLSULFONYL)OXAZIRIDINE
(2R,8AS)-(+)-(CAMPHORYLSULFONYL)OXAZIRIDINE
(+)-((CAMPHORYL)SULFONYL)OXAZIRIDINE
(S)-2,N-EPOXY-EXO-10,2-BORNANESULTAM
(S)-(+)-(CAMPHORSULFONYL)OXAZIRIDINE
(1S)-(+)-(10-Camphorsulfonyl)oxaziridine (1S)-(+)-2,N-Epoxy-exo-10,2-bornanesultam
(+)-(2R,8aS)-(Camphorylsulfonyl)oxaziridine, 99+% ee, 99+%
(S)-(+)-(Camphorsulfonyl)Oxazi
(1S)-(+)-(10-CAMPHORSULFONYL) OXAZIRINE
(2R 8AS)-(+)-(CAMPHORYLSULFONYL)OXAZIRIDINE [ASYMMETRIC OXIDIZING GR]
(2R,8aS)-(+)-(Camphorylsulfonyl)oxaziridine [Asymmetric Oxidizing Reagent]
(1S)-(+)-(Camphorylsulfonyl)oxaziridine, (1S)-(+)-2,N-Epoxy-exo-10,2-bornanesultam
(1α,5β,7α)-10,10-Dimethyl-4,5-epoxy-3-thia-4-azatricyclo[5.2.1.01,5]decane3,3-dioxide
(3aS)-9,9-Dimethyloctahydro-3aβ,6β-methano-1,7aα-epoxy-2,1-benzisothiazole 2,2-dioxide
(4aS,7R,8aS)-5,6,7,8-Tetrahydro-9,9-dimethyl-4H-4a,7-methanooxazirino[3,2-i][2,1]benzoisothiazole 3,3-dioxide
(4aS,7R,8aS)-9,9-Dimethyl-4H-4a,7-methanotetrahydrooxazirino[3,2-i][2,1]benzisothiazole 3,3-dioxide | [Molecular Formula]
C10H15NO3S | [MDL Number]
MFCD00075319 | [Molecular Weight]
229.3 | [MOL File]
104322-63-6.mol |
| Chemical Properties | Back Directory | [Appearance]
white crystall powder | [Melting point ]
172-174 °C(lit.)
| [alpha ]
45 º (c=2, chloroform) | [Boiling point ]
317.6±25.0 °C(Predicted) | [density ]
1.2486 (rough estimate) | [refractive index ]
1.5060 (estimate) | [storage temp. ]
2-8°C
| [solubility ]
Chloroform (Sparingly), Methanol (Slightly) | [form ]
Crystals or Crystalline Powder | [pka]
-11.75±0.40(Predicted) | [color ]
White | [optical activity]
[α]28/D +45°, c = 2 in chloroform | [Usage]
A useful synthetic intermediate. Used for asymmetric hydroxylation | [BRN ]
6274370 | [CAS DataBase Reference]
104322-63-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [F ]
10 | [HS Code ]
29309090 |
| Hazard Information | Back Directory | [Chemical Properties]
(1S)-(+)-(Camphorylsulfonyl)oxaziridine is white crystall powder
| [Uses]
(1S)-(+)-(Camphorylsulfonyl)oxaziridine is a useful synthetic intermediate. Used for asymmetric hydroxylation
| [Definition]
(1S)-(+)-(Camphorylsulfonyl)oxaziridine is a neutral, aprotic, electrophilic, and asymmetric oxidizing agents for the chemoselective oxidation of many nucleophilic substrates such as sulfides, enamines, enol esters, carbanions, and enolates.
| [Synthesis]
The enantiopure (1S)-(+)-(Camphorylsulfonyl)oxaziridine and (1R)-(-)-(10-Camphorsulfonyl)oxaziridine and [(8,8- dichlorocamphor)sulfonyl]oxaziridines (2) are commercially available. They can also be prepared on a large scale via the oxidation of corresponding camphorsulfonimines with buffered Potassium Monoperoxysulfate (Oxone) or buffered peracetic acid. Since oxidation takes place from the endo face of the C=N double bond, only a single oxaziridine isomer is obtained. The precursor camphorsulfonimines can be prepared in 3 steps (>80% yield) from inexpensive (+)- and (-)-10-Camphorsulfonic Acids. A variety of (camphorylsulfonyl)oxaziridine derivatives such as (2)-(4) are also readily available via the functionalization of the camphorsulfonimines followed by oxidation.
 | [References]
1. Mergelsberg, I.; Gala, D.; Scherer, D.; DiBenedetto, D.; Tanner TL 1992, 33, 161.
2. Davis, F. A.; Kumar, A.; Chen, B.-C. JOC 1991, 56, 1143.
3. Chen, B.-C.; Weismiller, M. C.; Davis, F. A.; Boschelli, D.; Empfield, J. R.; Smith, III, A. B. T 1991, 47, 173. |
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