Chemistry–A European Journal

Catalytic Asymmetric Formation of δ??Lactones from Unsaturated Acyl Halides

PS Tiseni, R Peters

Index: Tiseni, Paolo S.; Peters, Rene Chemistry - A European Journal, 2010 , vol. 16, # 8 p. 2503 - 2517

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Citation Number: 37

Abstract

Abstract Previously unexplored enantiopure zwitterionic ammonium dienolates have been utilized in this work as reactive intermediates that act as diene components in hetero-Diels– Alder reactions (HDAs) with aldehydes to produce optically active δ-lactones, subunits of numerous bioactive products. The dienolates were generated in situ from E/Z mixtures of α, β-unsaturated acid chlorides by use of a nucleophilic quinidine derivative and Sn (OTf) 2 ...