Stereoselective Synthesis of (3R,4S)-Statine Utilising the Iron Acetyl Complex 5-C5H5)Fe(CO)(PPh3)COOMe> as a Chiral Acetate Enolate Equivalent

Article abstract of DOI:10.1016/S0040-4020(01)88019-4

Diethylaluminium enolates derived from the iron acetyl complex <(η⁵-C5H5)Fe(CO)(PPh3)COMe> undergo highly diastereoselective aldol reactions with the homochiral aldehydes: N,N-dibenzyl valinal and N,N-dibenzyl leucinal.The diastereoselectivity is explained in terms of Masamune's model of double asymmetric induction using the concept of matched and mismatched pairs.The matched pair aldol product arising from the reaction with N,N-dibenzyl leucinal is converted into the known γ-amino-β-hydroxy acid, (3R,4S)-statine.