Highly regioselective decarboxylative Claisen rearrangement reactions of diallyl 2-sulfonylmalonates

Donald Craig; Mark I Lansdell; Simon E Lewis

doi:10.1016/j.tetlet.2007.08.130

Highly regioselective decarboxylative Claisen rearrangement reactions of diallyl 2-sulfonylmalonates

Donald Craig, Mark I Lansdell, Simon E Lewis

Department of Chemistry

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Abstract

The decarboxylative Claisen rearrangement of a range of substituted diallyl 2-sulfonylmalonates is described. The substrates are made by C-carboxylation of the corresponding allyl sulfonylacetates with allyl para-nitrophenyl carbonates. The reactions display a high degree of regioselectivity, with allylic substituents possessing electron-rich substituents at the allyl three-position rearranging preferentially.

Original language	English
Pages (from-to)	7861-7864
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	44
DOIs	https://doi.org/10.1016/j.tetlet.2007.08.130
Publication status	Published - 29 Oct 2007

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10.1016/j.tetlet.2007.08.130

Lewis_Tetrahedron-Letters_2007_48_44_7861.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 Volume 48, Issue 44, 29 October 2007, Pages 7861-7864, DOI 10.1016/j.tetlet.2007.08.130
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title = "Highly regioselective decarboxylative Claisen rearrangement reactions of diallyl 2-sulfonylmalonates",

abstract = "The decarboxylative Claisen rearrangement of a range of substituted diallyl 2-sulfonylmalonates is described. The substrates are made by C-carboxylation of the corresponding allyl sulfonylacetates with allyl para-nitrophenyl carbonates. The reactions display a high degree of regioselectivity, with allylic substituents possessing electron-rich substituents at the allyl three-position rearranging preferentially.",

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AU - Craig, Donald

AU - Lansdell, Mark I

AU - Lewis, Simon E

PY - 2007/10/29

Y1 - 2007/10/29

N2 - The decarboxylative Claisen rearrangement of a range of substituted diallyl 2-sulfonylmalonates is described. The substrates are made by C-carboxylation of the corresponding allyl sulfonylacetates with allyl para-nitrophenyl carbonates. The reactions display a high degree of regioselectivity, with allylic substituents possessing electron-rich substituents at the allyl three-position rearranging preferentially.

AB - The decarboxylative Claisen rearrangement of a range of substituted diallyl 2-sulfonylmalonates is described. The substrates are made by C-carboxylation of the corresponding allyl sulfonylacetates with allyl para-nitrophenyl carbonates. The reactions display a high degree of regioselectivity, with allylic substituents possessing electron-rich substituents at the allyl three-position rearranging preferentially.

UR - http://dx.doi.org/10.1016/j.tetlet.2007.08.130

U2 - 10.1016/j.tetlet.2007.08.130

DO - 10.1016/j.tetlet.2007.08.130

M3 - Article

SN - 0040-4039

VL - 48

SP - 7861

EP - 7864

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 44

ER -

Highly regioselective decarboxylative Claisen rearrangement reactions of diallyl 2-sulfonylmalonates

Abstract

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