Chemistry of oxaziridines. 18. Synthesis and enantioselective oxidations of the [(8, 8-dihalocamphoryl) sulfonyl] oxaziridines

…, MC Weismiller, CK Murphy, RT Reddy…

Index: Davis, Franklin A.; Weismiller, Michael C.; Murphy, Christopher K.; Reddy, R. Thimma; Chen, Band-Chi Journal of Organic Chemistry, 1992 , vol. 57, # 28 p. 7274 - 7285

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Citation Number: 114

Abstract

The synthesis and enantioselective oxidations of [(8, 8-dihalocamphoryl) sulfonyl] oxaziridines[8, 8-dichloro-1, 7, 7-trimethyl-2'-(phenylsulfonyl) spiro [bicyclo [2.2. 1] heptane- 2, 3'-oxazinidine]] 13 are reported. These reagents are prepared in two steps from the (camphorylsulfony1) imine 4 by treatment of the corresponding azaenolate with electrophilic halogen sources followed by biphasic oxidation of the resulting dihalo imine 6-9 with m- ...