An asymmetric, SmI2-mediated approach to γ-butyrolactones using a new, fluorous-tagged auxiliary

Johannes C. Vogel; Rebecca Butler; David J. Procter

doi:10.1016/j.tet.2008.08.110

An asymmetric, SmI₂-mediated approach to γ-butyrolactones using a new, fluorous-tagged auxiliary

Johannes C. Vogel, Rebecca Butler, David J. Procter

Research output: Contribution to journal › Article › peer-review

16 Citations (Scopus)

Abstract

A new, fluorous-tagged chiral auxiliary has been developed for the asymmetric, SmI₂-mediated coupling of aldehydes and α,β-unsaturated esters. γ-Butyrolactones are obtained in moderate to good isolated yield and in high enantiomeric excess. The fluorous tag allows the auxiliary to be conveniently recovered by fluorous solid-phase extraction (FSPE) and reused.

Original language	English
Pages (from-to)	11876-11883
Number of pages	8
Journal	Tetrahedron
Volume	64
Issue number	52
DOIs	https://doi.org/10.1016/j.tet.2008.08.110
Publication status	Published - 22 Dec 2008
Externally published	Yes

Keywords

Samarium
Radicals
Asymmetric
Fluorous
Lactones

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tet.2008.08.110

Cite this

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title = "An asymmetric, SmI2-mediated approach to γ-butyrolactones using a new, fluorous-tagged auxiliary",

abstract = "A new, fluorous-tagged chiral auxiliary has been developed for the asymmetric, SmI2-mediated coupling of aldehydes and α,β-unsaturated esters. γ-Butyrolactones are obtained in moderate to good isolated yield and in high enantiomeric excess. The fluorous tag allows the auxiliary to be conveniently recovered by fluorous solid-phase extraction (FSPE) and reused.",

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AU - Butler, Rebecca

AU - Procter, David J.

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Y1 - 2008/12/22

N2 - A new, fluorous-tagged chiral auxiliary has been developed for the asymmetric, SmI2-mediated coupling of aldehydes and α,β-unsaturated esters. γ-Butyrolactones are obtained in moderate to good isolated yield and in high enantiomeric excess. The fluorous tag allows the auxiliary to be conveniently recovered by fluorous solid-phase extraction (FSPE) and reused.

AB - A new, fluorous-tagged chiral auxiliary has been developed for the asymmetric, SmI2-mediated coupling of aldehydes and α,β-unsaturated esters. γ-Butyrolactones are obtained in moderate to good isolated yield and in high enantiomeric excess. The fluorous tag allows the auxiliary to be conveniently recovered by fluorous solid-phase extraction (FSPE) and reused.

KW - Samarium

KW - Radicals

KW - Asymmetric

KW - Fluorous

KW - Lactones

UR - https://www.scopus.com/pages/publications/56249106105

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DO - 10.1016/j.tet.2008.08.110

M3 - Article

AN - SCOPUS:56249106105

SN - 0040-4020

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SP - 11876

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