(3 + 3) Cycloaddition of Oxyallyl Cations with Nitrones: Diastereoselective Access to 1,2-Oxazinanes

Marie Cordier; Alexis Archambeau

doi:10.1021/acs.orglett.8b00617

(3 + 3) Cycloaddition of Oxyallyl Cations with Nitrones: Diastereoselective Access to 1,2-Oxazinanes

Marie Cordier
, Alexis Archambeau

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

Résumé

Oxyallyl cations are prepared in situ from readily available α-tosyloxy ketones and act as transient electrophilic partners in (3 + 3) cycloaddition with nitrones. Under mild conditions, this method provides a chemoselective and diastereoselective route to polysubstituted 1,2-oxazinanes. A stepwise process is proposed to rationalize the diastereoselectivity of this transformation.

langue originale	Anglais
Pages (de - à)	2265-2268
Nombre de pages	4
journal	Organic Letters
Volume	20
Numéro de publication	8
Les DOIs	https://doi.org/10.1021/acs.orglett.8b00617
état	Publié - 20 avr. 2018
Modification externe	Oui

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10.1021/acs.orglett.8b00617

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title = "(3 + 3) Cycloaddition of Oxyallyl Cations with Nitrones: Diastereoselective Access to 1,2-Oxazinanes",

abstract = "Oxyallyl cations are prepared in situ from readily available α-tosyloxy ketones and act as transient electrophilic partners in (3 + 3) cycloaddition with nitrones. Under mild conditions, this method provides a chemoselective and diastereoselective route to polysubstituted 1,2-oxazinanes. A stepwise process is proposed to rationalize the diastereoselectivity of this transformation.",

author = "Marie Cordier and Alexis Archambeau",

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AU - Archambeau, Alexis

PY - 2018/4/20

Y1 - 2018/4/20

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AB - Oxyallyl cations are prepared in situ from readily available α-tosyloxy ketones and act as transient electrophilic partners in (3 + 3) cycloaddition with nitrones. Under mild conditions, this method provides a chemoselective and diastereoselective route to polysubstituted 1,2-oxazinanes. A stepwise process is proposed to rationalize the diastereoselectivity of this transformation.

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DO - 10.1021/acs.orglett.8b00617

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(3 + 3) Cycloaddition of Oxyallyl Cations with Nitrones: Diastereoselective Access to 1,2-Oxazinanes

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