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Updated: Jan 29, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Acetylene-based two-step diastereoselective synthesis of bridgehead dihydro-oxadiazines using ketones and hydrazine
Elena Yu Schmidt1, Nadezhda V Semenova, Elena V Ivanova
1A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russian Federation. boris_trofimov@irioch.irk.ru.
Abstract:
Pharmaceutically related bridgehead dihydro-1,3,4-oxadiazines are synthesized in up to 94% yield by the acid-catalyzed diastereoselective reaction of hydrazine hydrate with 6,8-dioxabicyclo[3.2.1]octanes (6,8-DOBCOs), the products of the superbase-promoted self-organization of acetylene with ketones. The synthesis covers a diverse range of alkylaromatic ketones having F-, Cl-, Br-, alkoxy-, CF3- and aryl substituents in different positions of the aromatic rings.
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