(1S)-(+)-(Camphorylsulfonyl)oxaziridine Chemical Properties

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)

pka

-11.75±0.40(Predicted)

form 

Crystals or Crystalline Powder

color 

White

optical activity

[α]28/D +45°, c = 2 in chloroform

BRN 

6274370

CAS DataBase Reference

104322-63-6(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

F 

10

HS Code 

29309090

MSDS

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(1S)-(+)-(Camphorylsulfonyl)oxaziridine Usage And Synthesis

Chemical Properties

(1S)-(+)-(Camphorylsulfonyl)oxaziridine is white crystall powder

Uses

(1S)-(+)-(Camphorylsulfonyl)oxaziridine is a useful synthetic intermediate. Used for asymmetric hydroxylation

Uses

(1S)-(+)-(10-Camphorsulfonyl)oxaziridine can be used:

• To convert prochiral ketone enolates into optically active α-hydroxy ketones via enantioselective asymmetric oxidation.
• In the synthesis of thymidine oligonucleotides connected through pyrophosphates.
• In the asymmetric synthesis of proton pump inhibitors like (R)-Rabeprazole sodium and (R)-Lansoprazole sodium from the corresponding DBU salt of prochiral sulfide.
• In the preparation of phosphonoacetate and thiophosphonoacetate oligodeoxynucleotides by oxidizing the corresponding phosphinoacetate.

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.

(1S)-(+)-(Camphorylsulfonyl)oxaziridine(104322-63-6)Related Product Information

• (1S)-(+)-(Camphorylsulfonyl)oxaziridine
• 3-METHYLCYCLOHEXYLAMINE
• 2-Methylcyclohexylamine
• 2-CYCLOPENTYL-ETHYLAMINE
• Cyclopentylamine
• DL-Camphor
• Camphor
• (1R)-(-)-(10-Camphorsulfonyl)oxaziridine
• 2-Ethyl-1-hexanethiol
• BORNYLAMINE
• Ethanesulfonamide
• 1-HEXANESULFONAMIDE
• 4-04-00-00045 (Beilstein Handbook Reference)
• 1-PENTANESULFONAMIDE
• N-CYCLOHEXYLHYDROXYLAMINE
• PROPANE-1-SULFONAMIDE
• ISOTHIAZOLINE 1,1-DIOXIDE
• CYCLOHEXYLMETHYL MERCAPTAN