Diene-Transmissive Enantioselective Diels-Alder Reactions and Sequences Involving Substituted Dendralenes

Josemon George, Michael S. Sherburn*

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    6 Citations (Scopus)

    Abstract

    Readily available and stable substituted [3]dendralenes undergo highly chemo-, regio-, diastereo-, and enantioselective organocatalyzed Diels-Alder reactions with acrolein to form enantiomerically enriched cycloadducts. These monocycloadducts carry semicyclic dienes that undergo a second, substrate-controlled diastereoselective Diels-Alder reaction with a different dienophile to form 2-fold cycloadducts. Overall, annulated, functional group rich, chiral Δ1(9)-octalin building blocks are accessed in one-pot operations that significantly extend the preparative value of diene-transmissive Diels-Alder sequences since they offer products of regio- and stereochemistry complementary to those generated from the parent, unsubstituted [3]dendralene.

    Original languageEnglish
    Pages (from-to)14712-14723
    Number of pages12
    JournalJournal of Organic Chemistry
    Volume84
    Issue number22
    DOIs
    Publication statusPublished - 15 Nov 2019

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