Comparison of solid-phase and solution-phase chiral auxiliaries in the alkylation/iodolactonization sequence to γ-butyrolactones

Michael D. Price, Mark J. Kurth, Neil E. Schore

Research output: Contribution to journalArticle

26 Scopus citations

Abstract

Five prolinol-based chiral auxilaries have been compared for the stereoselective synthesis of γ-butyrolactones via the sequence of N-acylation, Cα-allylation, and iodolactonization under both solution-phase and solid-phase conditions. Comparisons of stereoselectivity of both the Cα-allylation and iodolactonization processes indicate that incorporation of a non-C2-symmetric auxiliary as a polymer cross-link gives results superior to those obtained either in solution or with other non-C2-symmetric auxiliaries and comparable to those observed using a polymer-supported pseudo-C2-symmetric auxiliary.

Original languageEnglish (US)
Pages (from-to)7769-7773
Number of pages5
JournalJournal of Organic Chemistry
Volume67
Issue number22
DOIs
StatePublished - Nov 1 2002

ASJC Scopus subject areas

  • Organic Chemistry

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