Diels-Alder cycloadditions of chiral butenolides with butadiene and isoprene: diastereofacial selectivity and regioselectivity

Rosa M. Ortuño, Montserrat Balleteros, Jordi Corbera, Francisco Sanchez-Ferrando, Josep Font

Research output: Contribution to journalArticleResearchpeer-review

30 Citations (Scopus)

Abstract

Chiral butenolides react with butadiene at 210° giving optically active bicyclic compounds with excellent diastereoselectivity, in good yields. Optical purity of the adducts has been verified either by chemical correlation and/or by the use of Eu(hfc)3. Reactions with isoprene at 125-220° afford 1:1 mixtures of regioisomers, selectivity being increased by the use of AlCl3 as catalyst, at lower temperatures. © 1988.
Original languageEnglish
Pages (from-to)1711-1719
JournalTetrahedron
Volume44
Issue number6
DOIs
Publication statusPublished - 1 Jan 1988

Fingerprint

Dive into the research topics of 'Diels-Alder cycloadditions of chiral butenolides with butadiene and isoprene: diastereofacial selectivity and regioselectivity'. Together they form a unique fingerprint.

Cite this