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Updated: Jul 25, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Camphor-based alpha-bromo ketones for the asymmetric darzens reaction
1Departamento de Quimica Organica, Facultad de Quimica, Universidad del Pais Vasco, Apdo 1072, 20080 San Sebastian, Spain, Organisch-chemisches Institut der Universitat Zurich, Winterthurerstrasse 190, CH-8057 Zurich, Swit.
Abstract:
(1R)-2-endo-Bromoacetyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol (endo-2-bromoacetylisoborneol) 4 and its trimethylsilyl ether 3 are presented as efficient reagents for the asymmetric Darzens reaction. From the alpha,beta-epoxy ketone adducts the chiral inductor camphor is removed, by treatment with ceric(IV) ammonium nitrate, to yield the corresponding epoxy acids which are isolated as their dicyclohexylammonium salts.
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