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

Open access

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

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

Research group

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

Commercial URLhttps://pubs.acs.org/doi/10.1021/acsorginorgau.1c00006

ISSN of the journal2694-247X

155views

73downloads

Creation2021/10/06 11:03:00

First validation2021/10/06 11:03:00

Update time2023/03/16 01:26:38

Status update2023/03/16 01:26:38

Last indexation2024/02/12 13:30:50

Archive ouverte UNIGE

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