Photochemical [2 + 2] cycloaddition of acetylene to chiral 2(5H)-furanones

Ramon Alibés, Pedro De March, Marta Figueredo, Josep Font, Xiaolin Fu, Marta Racamonde, Ángel Álvarez-Larena, Juan F. Piniella

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25 Citations (Scopus)

Abstract

The [2 + 2] photocycloaddition of acetylene to chiral 2(5H)-furanones was investigated. The influence on the chemical yield and facial diastereoselectivity of the substituent at the stereogenic center and also the effect of a 4-methyl group were evaluated. A mechanistic proposal based on a simple theoretical conformational analysis is presented. Using a C2-symmetric bis(lactone) as the substrate, a diastereomeric excess higher than 98% was found.
Original languageEnglish
Pages (from-to)1283-1289
JournalJournal of Organic Chemistry
Volume68
Issue number4
DOIs
Publication statusPublished - 21 Feb 2003

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