Diastereofacial selectivity in uncatalyzed Diels-Alder cycloadditions involving α,β-unsaturated esters and lactones with stereogenic centers containing oxygen functiionalities

Ramón Casas, Teodor Parella, Vicenç Branchadell, Antonio Oliva, Rosa M. Ortuño, André Guingant

Research output: Contribution to journalArticleResearchpeer-review

41 Citations (Scopus)

Abstract

Both experimental and theoretical studies on the Diels-Alder cycloadditions of dienophiles 1, 2 and 3 to different dienes show that the observed diastereofacial selectivity results from a combination of electronic and steric interactions. The traditional Felkin-Anh mode is not appropriate for these cases. Several new chiral synthetic building blocks have been prepared. © 1992.
Original languageEnglish
Pages (from-to)2659-2680
JournalTetrahedron
Volume48
Issue number13
DOIs
Publication statusPublished - 27 Mar 1992

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