Solvent Effects in Asymmetric Hetero Diels-Alder and Ene Reactions.

Mogens Johannsen, Karl Anker Jørgensen

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    Abstract

    The use of polar solvents such as nitromethane or 2-nitropropane leads to a significant improvement of the catalytic properties of a cationic copper-Lewis acid in the hetero Diels-Alder reaction of alkyl glyoxylates with dienes; The scope of a newly developed copper(II)-bisoxazoline catalyst for the hetero Diels-Alder reaction is demonstrated by the reaction of different dienes with alkyl glyoxylates in nitroalkane solvents with the formation of the hetero Diels-Alder adduct in high enantiomeric excess as the major product. The synthetic application of the reaction is exemplified by an improved synthesis of a highly interesting synthon for sesquiterpene lactones. Copyright (C) 1996 Elsevier Science Ltd
    Original languageEnglish
    JournalTetrahedron
    Volume52
    Issue number21
    Pages (from-to)7321-7328
    ISSN0040-4020
    DOIs
    Publication statusPublished - 1996

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