Tetrahedron

Studies on the α-acetylation of δ-valerolactone and ε-caprolactone

J Christoffers, H Oertling, P Fischer, W Frey

Index: Christoffers, Jens; Oertling, Heiko; Fischer, Peter; Frey, Wolfgang Tetrahedron, 2003 , vol. 59, # 21 p. 3769 - 3778

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Citation Number: 25

Abstract

The synthetic approach to α-acetylated δ-valero-(7a) and ε-caprolactone (7b) is reported. While 7a was isolated in 21% yield from the respective iodoester 5a by an alkylation sequence involving transesterification and Finkelstein reaction, 7b was not obtained from 5b but the dimer 8. Also transesterification and olefin ring closing metathesis (RCM) failed to prepare 7b. RCM resulted in the dimeric lactone 10, showing that the formation of 14- ...