Gold-catalysed synthesis of phosphonate-substituted oxetan-3-ones – an easy access to highly strained HWE reagents

Gold-catalysed synthesis of phosphonate-substituted oxetan-3-ones – an easy access to highly strained HWE reagents

A convenient approach for the attainment of strained phosphonate-substituted oxetan-3-ones, starting from easy to synthesise alkynyl phosphonates, is presented. With the aid of a pyridine- N -oxide, in a gold-catalysed step an α-oxo carbene species is generated as a key intermediate. After formal OH...

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Veröffentlicht in:Organic Chemistry Frontiers 2021-12, Vol.9 (1), p.117-122
Hauptverfasser: Tahir, Shaista, Wunsch, Jonas F., Rudolph, Matthias, Rominger, Frank, Hashmi, A. Stephen K.
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Sprache:eng
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Chemical synthesis
Gold
Organic chemistry
Phosphonates
Reagents
Substitutes
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container_issue 1
container_start_page 117
container_title Organic Chemistry Frontiers
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creator Tahir, Shaista
Wunsch, Jonas F.
Rudolph, Matthias
Rominger, Frank
Hashmi, A. Stephen K.
description A convenient approach for the attainment of strained phosphonate-substituted oxetan-3-ones, starting from easy to synthesise alkynyl phosphonates, is presented. With the aid of a pyridine- N -oxide, in a gold-catalysed step an α-oxo carbene species is generated as a key intermediate. After formal OH-insertion, synthetically useful HWE reagents can be attained. The synthetic utility of the obtained building blocks could be demonstrated, which yielded the 2-alkenyl oxetan-3-one scaffold in high yields after the HWE reaction.
doi_str_mv 10.1039/D1QO01214B
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source Royal Society Of Chemistry Journals 2008-
subjects Chemical synthesis
Gold
Organic chemistry
Phosphonates
Reagents
Substitutes
title Gold-catalysed synthesis of phosphonate-substituted oxetan-3-ones – an easy access to highly strained HWE reagents
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