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

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

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.

Original language	English
Pages (from-to)	981-986
Number of pages	6
Journal	Synlett
Volume	32
Issue number	10
DOIs	https://doi.org/10.1055/s-0040-1706038
Publication status	Published - 31 May 2021
Externally published	Yes

Keywords

azadienes
catalysis
cycloaddition
heterocycles
medium-sized rings
oxazocines

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10.1055/s-0040-1706038

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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.",

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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

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VL - 32

SP - 981

EP - 986

JO - Synlett

JF - Synlett

IS - 10

ER -

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

Abstract

Keywords

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