Nitrosobenzene

Abstract

Nitrosobenzene is a reagent used in many asymmetric syntheses with amazing results. It acts as an electrophile in catalytic enantioselective carbon-nitrogen and carbon-oxygen bond-forming reactions. It has received attention in recent years because of its high reactivity and regio- and stereoselectivities. In the presence of Lewis or ­Brønsted acid catalysts, enantioselective nitroso aldol or ­nitroso Diels-Alder reactions proceed under smooth conditions. [¹] Nitrosobenzene can be used in the aminoxylation of aldehydes and ketones, and the products are precursors of 1,2-amino alcohols, terminal diols [²] and allylic alcohols. [³] It can also be used in asymmetric desymmetrization of α-hydroxy ketones. [4] Others applications are described below. This reagent is stable, inexpensive and commercially available, all of which corroborate its use.