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Synlett 1999; 1999(10): 1639-1641
DOI: 10.1055/s-1999-2897
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Synthesis of Conjugated γ- and δ-Lactones from Aldehydes and Ketones via a Vinylation/Allylation-Ring Closing Metathesis-Oxidation Sequence

Miguel Carda* , Encarnación Castillo, Santiago Rodríguez, Santiago Uriel, J. Alberto Marco
  • *Depart. de Q. Inorgánica y Orgánica, Univ. Jaume I, Castellón, Spain; Fax (+ 34)-9 64-72 82 14; E-mail: mcarda@qio.uji.es
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Publication Date:
31 December 1999 (online)

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Nucleophilic C-vinylation or C-allylation of aldehydes and ketones followed by O-allylation of the obtained carbinols gave the corresponding allyl ethers. Ring-closing metathesis of the latter afforded cyclic ethers (dihydrofurans and dihydropyrans, respectively) which were then subjected to allylic oxidation to yield conjugated γ- and δ-lactones.

Barbier allylation - ring-closing metathesis - allylic oxidation - conjugated lactones