Ring-opening hydrofluorination of 2,3- and 3,4-epoxy amines by HBF 4·OEt2: Application to the asymmetric synthesis of (S, S)-3-deoxy-3-fluorosafingol

Alexander J. Cresswell; Stephen G. Davies; James A. Lee; Melloney J. Morris; Paul M. Roberts; James E. Thomson

doi:10.1021/jo200517w

Ring-opening hydrofluorination of 2,3- and 3,4-epoxy amines by HBF ₄·OEt₂: Application to the asymmetric synthesis of (S, S)-3-deoxy-3-fluorosafingol

Alexander J. Cresswell, Stephen G. Davies, James A. Lee, Melloney J. Morris, Paul M. Roberts, James E. Thomson

Department of Chemistry

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

23 Citations (SciVal)

Abstract

Treatment of a range of 2,3- and 3,4-epoxy amines with HBF ₄·OEt₂ at room temperature results in fast and efficient S_N2-type ring-opening hydrofluorination to give stereodefined amino fluorohydrins. Operational simplicity, scalability, and short reaction time at ambient temperature are notable features of this method. The utility of this methodology is exemplified in a concise asymmetric synthesis of (S,S)-3-deoxy-3-fluorosafingol.

Original language	English
Pages (from-to)	4617-4627
Number of pages	11
Journal	Journal of Organic Chemistry
Volume	76
Issue number	11
DOIs	https://doi.org/10.1021/jo200517w
Publication status	Published - 3 Jun 2011

ASJC Scopus subject areas

Organic Chemistry

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title = "Ring-opening hydrofluorination of 2,3- and 3,4-epoxy amines by HBF 4·OEt2: Application to the asymmetric synthesis of (S, S)-3-deoxy-3-fluorosafingol",

abstract = "Treatment of a range of 2,3- and 3,4-epoxy amines with HBF 4·OEt2 at room temperature results in fast and efficient SN2-type ring-opening hydrofluorination to give stereodefined amino fluorohydrins. Operational simplicity, scalability, and short reaction time at ambient temperature are notable features of this method. The utility of this methodology is exemplified in a concise asymmetric synthesis of (S,S)-3-deoxy-3-fluorosafingol.",

author = "Cresswell, {Alexander J.} and Davies, {Stephen G.} and Lee, {James A.} and Morris, {Melloney J.} and Roberts, {Paul M.} and Thomson, {James E.}",

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T1 - Ring-opening hydrofluorination of 2,3- and 3,4-epoxy amines by HBF 4·OEt2

T2 - Application to the asymmetric synthesis of (S, S)-3-deoxy-3-fluorosafingol

AU - Cresswell, Alexander J.

AU - Davies, Stephen G.

AU - Lee, James A.

AU - Morris, Melloney J.

AU - Roberts, Paul M.

AU - Thomson, James E.

PY - 2011/6/3

Y1 - 2011/6/3

N2 - Treatment of a range of 2,3- and 3,4-epoxy amines with HBF 4·OEt2 at room temperature results in fast and efficient SN2-type ring-opening hydrofluorination to give stereodefined amino fluorohydrins. Operational simplicity, scalability, and short reaction time at ambient temperature are notable features of this method. The utility of this methodology is exemplified in a concise asymmetric synthesis of (S,S)-3-deoxy-3-fluorosafingol.

AB - Treatment of a range of 2,3- and 3,4-epoxy amines with HBF 4·OEt2 at room temperature results in fast and efficient SN2-type ring-opening hydrofluorination to give stereodefined amino fluorohydrins. Operational simplicity, scalability, and short reaction time at ambient temperature are notable features of this method. The utility of this methodology is exemplified in a concise asymmetric synthesis of (S,S)-3-deoxy-3-fluorosafingol.

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JF - Journal of Organic Chemistry

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ER -

Ring-opening hydrofluorination of 2,3- and 3,4-epoxy amines by HBF ₄·OEt₂: Application to the asymmetric synthesis of (S, S)-3-deoxy-3-fluorosafingol

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