Iron Mediated Synthesis of 4-Amino-Enoates of High Enantiomeric Purity

Dieter Enders; Michael Finkam

doi:10.1055/s-1993-22470

Synlett 1993; 1993(6): 401-403
DOI: 10.1055/s-1993-22470

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Iron Mediated Synthesis of 4-Amino-Enoates of High Enantiomeric Purity

Dieter Enders^* , Michael Finkam

^*Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, D-5100 Aachen, Germany

Abstract

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The nucleophilic addition of various nitrogen nucleophiles to the highly enantiomerically enriched 1-methoxycarbonyl-3-methyl-(η³-allyl)-tetracarbonyliron-(1+)-tetrafluoroborate (2) (ee ≥ 95%) leads after oxidative removal of the tetracarbonyliron group to 4-aminoenoates (S)-3 of high enantiomeric purity (ee = 95-98%). The reaction is highly regio- and stereoselective and proceeds in good yields without isomerization of the double bond.

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