A Palladium-Catalyzed Oxa-(4+4)-Cycloaddition Strategy towards Oxazocine Scaffolds

Anaïs Scuiller; Xueyang Liu; Marie Cordier; Julian Garrec; Alexis Archambeau

doi:10.1055/s-0040-1706038

A Palladium-Catalyzed Oxa-(4+4)-Cycloaddition Strategy towards Oxazocine Scaffolds

Anaïs Scuiller
, Xueyang Liu
, Marie Cordier
, Julian Garrec
, Alexis Archambeau

Laboratoire de Synthèse Organique
CNRS
Unité Chimie et Procédés

Résultats de recherche: Contribution à un journal › Article › Revue par des pairs

Résumé

A Pd-catalyzed oxa-(4+4)-cycloaddition between 1-azadienes and (2-hydroxymethyl)allyl carbonates is described. Aurone-derived azadienes furnished polycyclic 1,5-oxazocines in good yields. Interestingly, linear azadienes have also been involved and yielded monocyclic heterocycles with complete regioselectivity. DFT calculations were carried out to gain insight on this observation.

langue originale	Anglais
Pages (de - à)	981-986
Nombre de pages	6
journal	Synlett
Volume	32
Numéro de publication	10
Les DOIs	https://doi.org/10.1055/s-0040-1706038
état	Publié - 31 mai 2021
Modification externe	Oui

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10.1055/s-0040-1706038

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title = "A Palladium-Catalyzed Oxa-(4+4)-Cycloaddition Strategy towards Oxazocine Scaffolds",

abstract = "A Pd-catalyzed oxa-(4+4)-cycloaddition between 1-azadienes and (2-hydroxymethyl)allyl carbonates is described. Aurone-derived azadienes furnished polycyclic 1,5-oxazocines in good yields. Interestingly, linear azadienes have also been involved and yielded monocyclic heterocycles with complete regioselectivity. DFT calculations were carried out to gain insight on this observation.",

keywords = "azadienes, catalysis, cycloaddition, heterocycles, medium-sized rings, oxazocines",

author = "Ana{\"i}s Scuiller and Xueyang Liu and Marie Cordier and Julian Garrec and Alexis Archambeau",

year = "2021",

month = may,

day = "31",

doi = "10.1055/s-0040-1706038",

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T1 - A Palladium-Catalyzed Oxa-(4+4)-Cycloaddition Strategy towards Oxazocine Scaffolds

AU - Scuiller, Anaïs

AU - Liu, Xueyang

AU - Cordier, Marie

AU - Garrec, Julian

AU - Archambeau, Alexis

PY - 2021/5/31

Y1 - 2021/5/31

N2 - A Pd-catalyzed oxa-(4+4)-cycloaddition between 1-azadienes and (2-hydroxymethyl)allyl carbonates is described. Aurone-derived azadienes furnished polycyclic 1,5-oxazocines in good yields. Interestingly, linear azadienes have also been involved and yielded monocyclic heterocycles with complete regioselectivity. DFT calculations were carried out to gain insight on this observation.

AB - A Pd-catalyzed oxa-(4+4)-cycloaddition between 1-azadienes and (2-hydroxymethyl)allyl carbonates is described. Aurone-derived azadienes furnished polycyclic 1,5-oxazocines in good yields. Interestingly, linear azadienes have also been involved and yielded monocyclic heterocycles with complete regioselectivity. DFT calculations were carried out to gain insight on this observation.

KW - azadienes

KW - catalysis

KW - cycloaddition

KW - heterocycles

KW - medium-sized rings

KW - oxazocines

UR - https://www.scopus.com/pages/publications/85106911109

U2 - 10.1055/s-0040-1706038

DO - 10.1055/s-0040-1706038

M3 - Article

AN - SCOPUS:85106911109

SN - 0936-5214

VL - 32

SP - 981

EP - 986

JO - Synlett

JF - Synlett

IS - 10

ER -

A Palladium-Catalyzed Oxa-(4+4)-Cycloaddition Strategy towards Oxazocine Scaffolds

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