β-Hydroxy esters: (E)- versus (Z)-enolate geometry in dianionic claisen rearrangements

Mark J. Kurth, Richard L. Beard

Research output: Contribution to journalArticle

20 Scopus citations

Abstract

Control elements operative in the β-hydroxy ester dianionic Claisen rearrangements are probed. Stereochemistry at Cβ dictates face selectivity at Cα and Cβ′ in 1 → 2-5, but only to the extent that it controls ester enolate geometry since a second important control element, chair/boat selectivity, is also operative. Evidence for excellent (E)-enolate selectivity in the enolization of β-hydroxy esters (cf. 7 and 13) and substrate-dependent chair/boat selectivity in the ensuing Claisen rearrangement are described.

Original languageEnglish (US)
Pages (from-to)4085-4088
Number of pages4
JournalJournal of Organic Chemistry
Volume53
Issue number17
StatePublished - 1988

ASJC Scopus subject areas

  • Organic Chemistry

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