[2+2] photocycloaddition of homochiral 2(5H)-furanones to alkenes. First step for an efficient and diastereoselective synthesis of (+)- and (-)-grandisol

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Abstract

The [2+2] photocycloaddition of homochiral 5-alkyl-2(5H)-furanones to alkenes is studied in order to evaluate the influence of the stereogenic centre to induce facial diastereoselectivity. The major cycloadduct could be transformed, eventually, in (+)-grandisol. The existence of a charge-transfer complex between the furanone and electron rich substituted alkenes as well as the formation of a predominant conformation in 5-oxyalkylfuranones due to n-π interactions are discussed.
Original languageEnglish
Pages (from-to)1267-1278
JournalTetrahedron
Volume52
Issue number4
DOIs
Publication statusPublished - 1 Jan 1996

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