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

doi:10.1021/jo0260692

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

Chemistry

Research output: Contribution to journal › Article

26 Citations (Scopus)

Abstract

Five prolinol-based chiral auxilaries have been compared for the stereoselective synthesis of γ-butyrolactones via the sequence of N-acylation, C_α-allylation, and iodolactonization under both solution-phase and solid-phase conditions. Comparisons of stereoselectivity of both the C_α-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 language	English (US)
Pages (from-to)	7769-7773
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	67
Issue number	22
DOIs	https://doi.org/10.1021/jo0260692
State	Published - Nov 1 2002

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Allylation

Alkylation

Polymers

Stereoselectivity

Acylation

ASJC Scopus subject areas

Organic Chemistry

Cite this

Price, M. D., Kurth, M. J., & Schore, N. E. (2002). Comparison of solid-phase and solution-phase chiral auxiliaries in the alkylation/iodolactonization sequence to γ-butyrolactones. Journal of Organic Chemistry, 67(22), 7769-7773. https://doi.org/10.1021/jo0260692

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 journal › Article

Price, MD, Kurth, MJ & Schore, NE 2002, 'Comparison of solid-phase and solution-phase chiral auxiliaries in the alkylation/iodolactonization sequence to γ-butyrolactones', Journal of Organic Chemistry, vol. 67, no. 22, pp. 7769-7773. https://doi.org/10.1021/jo0260692

Price MD, Kurth MJ, Schore NE. Comparison of solid-phase and solution-phase chiral auxiliaries in the alkylation/iodolactonization sequence to γ-butyrolactones. Journal of Organic Chemistry. 2002 Nov 1;67(22):7769-7773. https://doi.org/10.1021/jo0260692

Price, Michael D. ; Kurth, Mark J. ; Schore, Neil E. / Comparison of solid-phase and solution-phase chiral auxiliaries in the alkylation/iodolactonization sequence to γ-butyrolactones. In: Journal of Organic Chemistry. 2002 ; Vol. 67, No. 22. pp. 7769-7773.

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