Organic Letters 2007-10-25

Efficient preparation of N-phenylsulfenyl ketimines from oximes or nitro compounds without racemization of alpha-stereocenters.

Jordi Burés, Carles Isart, Jaume Vilarrasa

Index: Org. Lett. 9(22) , 4635-4638, (2007)

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Abstract

As N-sulfenyl imines (e.g., RR'C=N-SAr) can be readily transformed to their N-sulfinyl imines (RR'C=N-SOAr), N-sulfonyl imines (RR'C=N-SO2Ar), and N-sulfonyl oxaziridines, the very mild procedure developed to convert ketoximes and secondary nitro derivatives to N-arenesulfenyl ketimines constitutes a new and efficient route to all these series of compounds. The configuration of the alpha-stereocenters is retained.