A synthetic alternative to the Type-II intramolecular 4+3 cycloaddition reaction

Richard Grainger; RB Owoare; P Tisselli; JW Steed

doi:10.1021/jo034356f

A synthetic alternative to the Type-II intramolecular 4+3 cycloaddition reaction

Richard Grainger
, RB Owoare
, P Tisselli
, JW Steed

Chemistry

Research output: Contribution to journal › Article

34 Citations (Scopus)

Abstract

Oxyallyl cations generated in situ from dihaloketones have been found to undergo the Favorskii rearrangement in preference to an intramolecular Type-II 4 + 3 cycloaddition reaction in trifluoroethanol and hexafluoropropan-2-ol solvents, generating acrylate esters with high cis selectivity. A synthetic alternative to the intramolecular Type-II 4 + 3 cycloaddition has been developed on the basis of intramolecular enolate alkylation to close a 7-membered ring with an exocyclic double bond.

Original language	English
Pages (from-to)	7899-7902
Number of pages	4
Journal	The Journal of Organic Chemistry
Volume	68
Issue number	20
Early online date	9 Sept 2003
DOIs	https://doi.org/10.1021/jo034356f
Publication status	Published - 1 Oct 2003

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abstract = "Oxyallyl cations generated in situ from dihaloketones have been found to undergo the Favorskii rearrangement in preference to an intramolecular Type-II 4 + 3 cycloaddition reaction in trifluoroethanol and hexafluoropropan-2-ol solvents, generating acrylate esters with high cis selectivity. A synthetic alternative to the intramolecular Type-II 4 + 3 cycloaddition has been developed on the basis of intramolecular enolate alkylation to close a 7-membered ring with an exocyclic double bond.",

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AU - Owoare, RB

AU - Tisselli, P

AU - Steed, JW

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N2 - Oxyallyl cations generated in situ from dihaloketones have been found to undergo the Favorskii rearrangement in preference to an intramolecular Type-II 4 + 3 cycloaddition reaction in trifluoroethanol and hexafluoropropan-2-ol solvents, generating acrylate esters with high cis selectivity. A synthetic alternative to the intramolecular Type-II 4 + 3 cycloaddition has been developed on the basis of intramolecular enolate alkylation to close a 7-membered ring with an exocyclic double bond.

AB - Oxyallyl cations generated in situ from dihaloketones have been found to undergo the Favorskii rearrangement in preference to an intramolecular Type-II 4 + 3 cycloaddition reaction in trifluoroethanol and hexafluoropropan-2-ol solvents, generating acrylate esters with high cis selectivity. A synthetic alternative to the intramolecular Type-II 4 + 3 cycloaddition has been developed on the basis of intramolecular enolate alkylation to close a 7-membered ring with an exocyclic double bond.

UR - https://www.scopus.com/pages/publications/0141765909

U2 - 10.1021/jo034356f

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M3 - Article

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SP - 7899

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JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

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ER -

A synthetic alternative to the Type-II intramolecular 4+3 cycloaddition reaction

Abstract

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