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NFPA 704
1
0
0
(1R)-(-)-(10-캄포르술포닐)옥사지리딘 C화학적 특성, 용도, 생산
화학적 성질
White crystalline powder
용도
(1R)-(-)-(10-Camphorsulfonyl)oxaziridine is a useful synthetic intermediate. Used for asymmetric hydroxylation.
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.
