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

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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

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Allylation
Alkylation
Polymers
Stereoselectivity
Acylation

ASJC Scopus subject areas

  • Organic Chemistry

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Comparison of solid-phase and solution-phase chiral auxiliaries in the alkylation/iodolactonization sequence to γ-butyrolactones. / Price, Michael D.; Kurth, Mark J.; Schore, Neil E.

In: Journal of Organic Chemistry, Vol. 67, No. 22, 01.11.2002, p. 7769-7773.

Research output: Contribution to journalArticle

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