Tsuji-Trost Based Cascades: From Passerini Adducts of Cinnamaldehyde to Allylated Oxazolones

Elhachemia Elmamouni; Marianne Guillard; Baptiste Haddou; Laurence Grimaud; Laurent El Kaïm

doi:10.1021/acs.joc.3c02169

Tsuji-Trost Based Cascades: From Passerini Adducts of Cinnamaldehyde to Allylated Oxazolones

Elhachemia Elmamouni
, Marianne Guillard
, Baptiste Haddou
, Laurence Grimaud
, Laurent El Kaïm

Research output: Contribution to journal › Article › peer-review

Abstract

The Passerini coupling of cinnamaldehyde derivatives affords allylic esters that may behave as both electrophiles and nucleophiles in Tsuji-Trost reactions. We present herein the interaction of the latter with methylallylcarbonate, leading to the formation of oxazolidine-diones. The efficiency of the process relies on the building up of a CO₂ overpressure in the medium. A reaction mechanism highlighting the reversibility of the Tsuji-Trost reaction is proposed for the process.

Original language	English
Pages (from-to)	2009-2013
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	89
Issue number	3
DOIs	https://doi.org/10.1021/acs.joc.3c02169
Publication status	Published - 2 Feb 2024
Externally published	Yes

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10.1021/acs.joc.3c02169

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title = "Tsuji-Trost Based Cascades: From Passerini Adducts of Cinnamaldehyde to Allylated Oxazolones",

abstract = "The Passerini coupling of cinnamaldehyde derivatives affords allylic esters that may behave as both electrophiles and nucleophiles in Tsuji-Trost reactions. We present herein the interaction of the latter with methylallylcarbonate, leading to the formation of oxazolidine-diones. The efficiency of the process relies on the building up of a CO2 overpressure in the medium. A reaction mechanism highlighting the reversibility of the Tsuji-Trost reaction is proposed for the process.",

author = "Elhachemia Elmamouni and Marianne Guillard and Baptiste Haddou and Laurence Grimaud and \{El Ka{\"i}m\}, Laurent",

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T2 - From Passerini Adducts of Cinnamaldehyde to Allylated Oxazolones

AU - Elmamouni, Elhachemia

AU - Guillard, Marianne

AU - Haddou, Baptiste

AU - Grimaud, Laurence

AU - El Kaïm, Laurent

PY - 2024/2/2

Y1 - 2024/2/2

N2 - The Passerini coupling of cinnamaldehyde derivatives affords allylic esters that may behave as both electrophiles and nucleophiles in Tsuji-Trost reactions. We present herein the interaction of the latter with methylallylcarbonate, leading to the formation of oxazolidine-diones. The efficiency of the process relies on the building up of a CO2 overpressure in the medium. A reaction mechanism highlighting the reversibility of the Tsuji-Trost reaction is proposed for the process.

AB - The Passerini coupling of cinnamaldehyde derivatives affords allylic esters that may behave as both electrophiles and nucleophiles in Tsuji-Trost reactions. We present herein the interaction of the latter with methylallylcarbonate, leading to the formation of oxazolidine-diones. The efficiency of the process relies on the building up of a CO2 overpressure in the medium. A reaction mechanism highlighting the reversibility of the Tsuji-Trost reaction is proposed for the process.

UR - https://www.scopus.com/pages/publications/85182581595

U2 - 10.1021/acs.joc.3c02169

DO - 10.1021/acs.joc.3c02169

M3 - Article

AN - SCOPUS:85182581595

SN - 0022-3263

VL - 89

SP - 2009

EP - 2013

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 3

ER -

Tsuji-Trost Based Cascades: From Passerini Adducts of Cinnamaldehyde to Allylated Oxazolones

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