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2005
Esterification
O 0315
Conversion of α,β-Unsaturated Aldehydes into Saturated Esters: An Umpolung
Catalyzed by Nucleophilic Carbenes. — The combination of the title alde29- 063 Reaction
hydes and N-heterocyclic carbenes, generated in situ from benzimidazolium salt,
allows the access of the unusual homoenolate reactivity under catalytic conditions. The
unique nucleophilic species possesses subsequent electrophilic character at the carbonyl carbon that is trapped by a secondary nucleophile such as an alcohol. The combination of a proton donor and a separate nucleophile affords the highest yields of the
resulting saturated esters. The use of a chiral imidazoylidene carbene as a catalyst in
the reaction allows for the kinetic resolution of chiral secondary alcohols. — (CHAN,
A.; SCHEIDT*, K. A.; Org. Lett. 7 (2005) 5, 905-908; Dep. Chem., Northwest. Univ.,
Evanston, IL 60208, USA; Eng.) — Steudel
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