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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
A strong hydride donating, acid stable and reusable 1,4-dihydropyridine for selective aldimine and aldehyde
Yasukazu Hirao1, Hajime Eto1, Mitsuru Teraoka1
1Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan. y-hirao@chem.sci.osaka-u.ac.jp.
Abstract:
A 1,4-dihydropyridine derivative, lacking carbonyl groups and containing bulky aryl substituents, was synthesized and found to have a high hydride donating ability, acid resistance and reusability. Thermodynamic parameters for electron and hydride transfer in the redox system comprising the 1,4-dihydropyridine and its corresponding pyridinium ion were determined. In addition, studies showed that the 1,4-dihydropyridine with steric hindrance can be used to promote efficient, boron trifluoride catalyzed selective reduction reactions of aldimines and aldehydes under mild conditions.
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