Ireland-Claisen rearrangement of substrates bearing chiral enol ether units

James P Tellam; David R Carbery

doi:10.1016/j.tetlet.2011.09.011

Ireland-Claisen rearrangement of substrates bearing chiral enol ether units

James P Tellam, David R Carbery

Department of Chemistry

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Abstract

The Ireland-Claisen [3,3]-sigmatropic rearrangement of an allylic glycinate bearing a remote chiral enol ether has been studied. Remote exopericyclic stereocontrol is achievable in this instance. The product from this rearrangement has been progressed through a formal total synthesis of the natural antibiotic, furanomycin.

Original language	English
Pages (from-to)	6027-6029
Number of pages	3
Journal	Tetrahedron Letters
Volume	52
Issue number	45
DOIs	https://doi.org/10.1016/j.tetlet.2011.09.011
Publication status	Published - 9 Nov 2011

Keywords

sigmatropic
amino acid
furanomycin
rearrangement
Ireland-Claisen

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10.1016/j.tetlet.2011.09.011

Carbery_Tetrahedron-Letters_2011_52_45_6027.pdf
NOTICE: this is the author’s version of a work that was accepted for publication in Tetrahedron Letters. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Tetrahedron Letters, vol 52, issue 45, 2011, DOI 10.1016/j.tetlet.2011.09.011
Accepted author manuscript, 372 KB

Cite this

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title = "Ireland-Claisen rearrangement of substrates bearing chiral enol ether units",

abstract = "The Ireland-Claisen [3,3]-sigmatropic rearrangement of an allylic glycinate bearing a remote chiral enol ether has been studied. Remote exopericyclic stereocontrol is achievable in this instance. The product from this rearrangement has been progressed through a formal total synthesis of the natural antibiotic, furanomycin.",

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AU - Carbery, David R

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AB - The Ireland-Claisen [3,3]-sigmatropic rearrangement of an allylic glycinate bearing a remote chiral enol ether has been studied. Remote exopericyclic stereocontrol is achievable in this instance. The product from this rearrangement has been progressed through a formal total synthesis of the natural antibiotic, furanomycin.

KW - sigmatropic

KW - amino acid

KW - furanomycin

KW - rearrangement

KW - Ireland-Claisen

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JF - Tetrahedron Letters

IS - 45

ER -

Ireland-Claisen rearrangement of substrates bearing chiral enol ether units

Abstract

Keywords

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