Nucleophilic Trapping of Alkoxy-Stabilized Oxyallyl Systems Generated from Inosose 2-O-Mesylates

Kieran Stockton; Stephen Glover; Ben Greatrex

doi:10.1055/s-0034-1379490

Nucleophilic Trapping of Alkoxy-Stabilized Oxyallyl Systems Generated from Inosose 2-O-Mesylates

Kieran Stockton, Stephen Glover, Ben Greatrex

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2 Citations (Scopus)

Abstract

Protected inosose 2-O-mesylates generate oxyallyl systems by elimination of the mesylate group after enolization. The reaction is promoted by weak bases such as triethylamine and azide, and the oxyallyl systems are then trapped by nucleophilic alcohols or azide. Computations using DFT/B3LYP confirm that the singlet planar oxyallyl is stabilized by the exocyclic alkoxy group.

Original language	English
Pages (from-to)	111-115
Journal	Synlett
Volume	26
Issue number	1
DOIs	https://doi.org/10.1055/s-0034-1379490
Publication status	Published - 2015

Keywords

Natural Products Chemistry
Organic Chemical Synthesis
Physical Organic Chemistry

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https://hdl.handle.net/1959.11/16535

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title = "Nucleophilic Trapping of Alkoxy-Stabilized Oxyallyl Systems Generated from Inosose 2-O-Mesylates",

abstract = "Protected inosose 2-O-mesylates generate oxyallyl systems by elimination of the mesylate group after enolization. The reaction is promoted by weak bases such as triethylamine and azide, and the oxyallyl systems are then trapped by nucleophilic alcohols or azide. Computations using DFT/B3LYP confirm that the singlet planar oxyallyl is stabilized by the exocyclic alkoxy group.",

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author = "Kieran Stockton and Stephen Glover and Ben Greatrex",

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AU - Glover, Stephen

AU - Greatrex, Ben

PY - 2015

Y1 - 2015

N2 - Protected inosose 2-O-mesylates generate oxyallyl systems by elimination of the mesylate group after enolization. The reaction is promoted by weak bases such as triethylamine and azide, and the oxyallyl systems are then trapped by nucleophilic alcohols or azide. Computations using DFT/B3LYP confirm that the singlet planar oxyallyl is stabilized by the exocyclic alkoxy group.

AB - Protected inosose 2-O-mesylates generate oxyallyl systems by elimination of the mesylate group after enolization. The reaction is promoted by weak bases such as triethylamine and azide, and the oxyallyl systems are then trapped by nucleophilic alcohols or azide. Computations using DFT/B3LYP confirm that the singlet planar oxyallyl is stabilized by the exocyclic alkoxy group.

KW - Natural Products Chemistry

KW - Organic Chemical Synthesis

KW - Physical Organic Chemistry

UR - https://www.scopus.com/pages/publications/84919655640

U2 - 10.1055/s-0034-1379490

DO - 10.1055/s-0034-1379490

M3 - Article

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JO - Synlett

JF - Synlett

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ER -

Nucleophilic Trapping of Alkoxy-Stabilized Oxyallyl Systems Generated from Inosose 2-O-Mesylates

Abstract

Keywords

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