Tetrahedron

Photodeconjugaison enantioelective d'esters et de lactones conjuguees en presence d'ephedrine

F Henin, R Mortezaei, J Muzart, JP Pete, O Piva

Index: Henin, Francoise; Mortezaei, Reza; Muzart, Jacques; Pete, Jean-Pierre; Piva, Oliverier Tetrahedron, 1989 , vol. 45, # 19 p. 6171 - 6196

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Citation Number: 19

Abstract

α, β-unsaturated esters and α-alkylidene lactones bearing one γ-hydrogen on the unsaturated chain, were deconjugated by irradiation with UV light (λ= 254 nm). When the reaction was carried out in the presence of (+) or (−) ephedrine, an enantioselective C- protonation of the photodienolic intermediate led to the deconjugated ester with an enantiomeric excess up to 30%. The scope of the reaction and the configuration of the ...