L. H. Meuer, C. Johannes, Van Niel
1984
Citations
0
Influential Citations
21
Citations
Journal
Tetrahedron
Abstract
Abstract N-(Cyclopropylmethylene)phenylamines (1a-c), cyclopropyl 2-pyridyl ketones (5-c) and ethyl cyclopropylmethlenepyruvate (14) have been subjected to reduction by l,4-dihydropyridines [3,5-diethoxycarbonyl-2,6-dimethyl-l,4-dihydropyridine (2) and/or 1-benzyl-1,4-dihydronicotinamide (7)]in the presence of magnesium ions, and by tin hydrides. The reactions with 1,4-dihydropyridines do not involve cleavage of the three-membered ring in the reduction step. The observed acyclic product from 2-pyridyl 2,2-dimethylcyclopropyl ketone (5b) is a consequence of ring cleavage prior to reduction of the carbonyl function. In contrast, reduction of 1a-c and 5-c by tin hydrides leads to products in which the cylopropane moiety has undergone ring-opening. These findings support a hydride transfer mechanism for reductions with NADH models.