Tetrahedron p. 5185 - 5196 (1984)
Update date:2022-08-03
Topics:
Meijer, Louis H. P.
van Niel, Johannes C. G.
Pandit, Upendra K.
N-(Cyclopropylmethylene)phenylamines (1a-c), cyclopropyl 2-pyridyl ketones (5a-c) and ethyl cyclopropylmethylenepyruvate (14) have been subjected to reduction by 1,4-dihydropyridines <3,5-diethoxycarbonyl-2,6-dimethyl-1,4-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 5a-c by tin hydrides leads to products in which the cyclopropane moiety has undergone ring-opening.These findings support a hydride transfer mechanism for reductions with NADH models.
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