Diastereoselective Formation of an [η⁴-(1<i>Z</i>)-Sulfinyl diene]iron(0) Tricarbonyl Complex. Diastereoselective Allylation of the Derived Iron Dienal

Abstract

An enantiomerically pure (1Z,3E)-sulfinyl diene exhibited a high degree of facial selectivity (α:β = 16:1) upon complexation to an iron(0) tricarbonyl fragment, producing a [η4-(1Z)-sulfinyl diene]iron(0) tricarbonyl complex (2; 80%). The iron(0)−dienal complex derived from 2 can undergo a highly diastereoselective allylation with allyltri-n-butylstannane and BF3·Et2O (diastereomer ratio 95:5); the absolute stereochemistry of the homoallylic alcohol product (4) was established by X-ray crystallography.