Enabling Cyclization Strategies through Carbonyl-Ylide-Mediated Synthesis of Malonate Enol Ethers

Vinas, Julia; Levitre, Guillaume; de Aguirre, Adiran; Besnard, Céline; Poblador Bahamonde, Amalia Isabel; Lacour, Jérôme

doi:10.1021/acsorginorgau.1c00006

Scientific article

English

Enabling Cyclization Strategies through Carbonyl-Ylide-Mediated Synthesis of Malonate Enol Ethers

ContributorsVinas, Julia; Levitre, Guillaume; de Aguirre, Adiran

; Besnard, Céline

; Poblador Bahamonde, Amalia Isabel

; Lacour, Jérôme

Published inACS Organic & Inorganic Au, vol. 1, no. 1, p. 11-17

Publication date2021-10-06

First online date2021-05-05

Abstract

Malonate enol ethers are afforded in one step by condensation of cyclic ketones with α-diazomalonates under [CpRu(CH3CN)3][BArF] catalysis. The dual reactivity of these 2-vinyloxymalonates can be used to expand the classical range of cyclizations derived from carbonyl ylide intermediates.

Keywords

Carbonyl ylide reactivity
CpRu catalysis
Diazo decomposition
Enol ethers
Malonate

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Research groups

Citation (ISO format)

VINAS, Julia et al. Enabling Cyclization Strategies through Carbonyl-Ylide-Mediated Synthesis of Malonate Enol Ethers. In: ACS Organic & Inorganic Au, 2021, vol. 1, n° 1, p. 11–17. doi: 10.1021/acsorginorgau.1c00006

Article (Published version)

CC BY-NC-ND

Identifiers

PID : unige:155213
DOI : 10.1021/acsorginorgau.1c00006

Additional URL for this publicationhttps://pubs.acs.org/doi/10.1021/acsorginorgau.1c00006

Journal ISSN2694-247X

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131downloads

Creation06/10/2021 13:03:00

First validation06/10/2021 13:03:00

Update time16/03/2023 02:26:38

Status update16/03/2023 02:26:38

Last indexation01/11/2024 00:17:29

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Enabling Cyclization Strategies through Carbonyl-Ylide-Mediated Synthesis of Malonate Enol Ethers

Malonate enol ethers are afforded in one step by condensation of cyclic ketones with α-diazomalonates under [CpRu(CH3CN)3][BArF] catalysis. The dual reactivity of these 2-vinyloxymalonates can be used to expand the classical range of cyclizations derived from carbonyl ylide intermediates.

Technical informations