Abstract
Bis(1,4-dihydro-1-pyridyl)zinc and -magnesium complexes are mild reducing agents. These compounds contain metal-bound 1,4-dihydropyridyl groups which act as hydride donors. In this paper we report the reactions of these new reagents with compounds which contain a carbonyl group, viz. ketones, aldehydes, enones and carboxylic esters. The stereochemistry of the reduction of cyclic ketones by bis(1,4-dihydro-1-pyridyl)zinc and -magnesium complexes has been studied. In reactions with carboxylic esters no reduction was observed; instead, acylation of one of the 1,4-dihydropyridyl groups bound to the metal took place yielding (novel) N-acyl-1,4-dihydropyridines. The scope of the reductions by the bis(1,4-dihydro-1-pyridyl)metal complexes is outlined, and the possible biological implications of the study are discussed.
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