Diastereoselective protonation of extended pyrrol-3-en-2-one enolates: An attempted 'de-epimerisation'

Jonathan Clayden, Rachel Turnbull, Ivan Pinto

    Research output: Contribution to journalArticlepeer-review

    Abstract

    The extended cyclic enolate derived from a simple pyrrol-3-en-2-one (butenolactam) was deuterated at the 5-position with very high diastereoselectivity if the nitrogen atom carries an α-methyl-p- methoxybenzyl group. A similar diastereoselective protonation was observed in a pyrrol-3-en-2-one formed by dearomatising cyclisation of a pyrrole. Protonation of an N-α-methyl-p-methoxybenzyl dihydroisoindolone lacked stereoselectivity. © 2005 Elsevier Ltd. All rights reserved.
    Original languageEnglish
    Pages (from-to)2235-2241
    Number of pages6
    JournalTetrahedron Asymmetry
    Volume16
    Issue number13
    DOIs
    Publication statusPublished - 4 Jul 2005

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