AuBr3-Catalyzed Thiooxime-to-Carbonyl Conversion: From Chiral Aliphatic Nitro Compounds to Ketones without Racemization

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A new variant of the NO2-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-H2O at pH 7, by addition of AuBr3 (but not with other MXn!). Adducts arising from asymmetric nitro-Michael and nitro-aldol reactions afford 1,4-diketones and alpha-alkoxy ketones, respectively, with full retention of the configuration of the stereocenters a to the CHNO2/C=N-SPh/C=O groups.

Bibliographical metadata

Original languageEnglish
Pages (from-to)4414-4417
Number of pages4
JournalOrganic Letters
Publication statusPublished - 2009