Efficient preparation of N-phenylsulfenyl ketimines from oximes or nitro compounds without racemization of alpha-stereocenters.
نویسندگان
چکیده
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.
منابع مشابه
AuBr3-catalyzed thiooxime-to-carbonyl conversion: from chiral aliphatic nitro compounds to ketones without racemization.
A new variant of the NO(2)-to-CO transformation (the Nef reaction) that occurs at room temperature under neutral conditions is uncovered. After the conversion of secondary nitroalkanes to phenylsulfenylketimines, these thiooximes are hydrolyzed quantitatively in situ, in THF-H(2)O at pH 7, by addition of AuBr(3) (but not with other MX(n)!). Adducts arising from asymmetric nitro-Michael and nitr...
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ورودعنوان ژورنال:
- Organic letters
دوره 9 22 شماره
صفحات -
تاریخ انتشار 2007