期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 138, 期 8, 页码 2670-2677出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b11796
关键词
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资金
- Deutsche Forschungsgemeinschaft (DFG), Priority Program Control of London dispersion interaction in molecular chemistry [SPP 1807, BE 998/14-1]
- Fonds der Chemischen Industrie
- BASF SE
As reported by Scheidt and Bode in 2005, sterically nonencumbered alpha,beta-enals are readily converted to saturated esters in the presence of alcohols and N-heterocyclic carbene catalysts, e.g., benzimidazolylidenes or triazolylidenes. However, substituents at the alpha- or beta-position of the alpha,beta-enal substrate are typically not tolerated, thus severely limiting the substrate spectrum. On the basis of our earlier mechanistic studies, a set of N-Mes- or N-Dipp-substituted 1,2,4-triazolium salts were synthesized and evaluated as (pre)catalysts in the redox esterification of various alpha- or beta-substituted enals. In particular the 1,4-bis-Mes/Dipp-1,2,4-triazolylidenes overcome the above limitations and efficiently catalyze the redox esterification of a whole series of alpha/beta-substituted enals hitherto not amenable to NHC-catalyzed transformations. The synthetic value of 1,4-bis-Mes/Dipp-1,2,4-triazolylidenes is further demonstrated by the one-step bicyclization of 10-oxocitral to (racemic) nepetalactone in diastereomerically pure form.
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