A strong hydride donating, acid stable and reusable 1, 4-dihydropyridine for selective aldimine and aldehyde reductions. Issue 8 (8th February 2022)

• Record Type: Journal Article
• Authors: Hirao, Yasukazu; Eto, Hajime; Teraoka, Mitsuru; Kubo, Takashi
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 8(2022)
• Page Start: 1671
• Page End: 1679
• Publication Date: 2022-02-08
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob02358f
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A new sterically protected 1, 4-dihydropyridine is a stable and regeneratable hydride donor in Brønsted and Lewis acid catalyzed reductions of aldimines and aldehydes. 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.