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

Jonathan Clayden*, Rachel Turnbull, Ivan Pinto

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

20 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)2235-2241
Number of pages7
JournalTetrahedron: Asymmetry
Volume16
Issue number13
DOIs
Publication statusPublished - 4 Jul 2005

Fingerprint Dive into the research topics of 'Diastereoselective protonation of extended pyrrol-3-en-2-one enolates: An attempted 'de-epimerisation''. Together they form a unique fingerprint.

  • Cite this