A General Method for the Vinylation of Nitrones. Synthesis of Allyl Hydroxylamines and Allyl Amines

Pedro Merino Departamento de Química Orgánica, ICMA, Facultad de Ciencias, Universidad de Zaragoza, E-50009, Aragon, Spain Fax: E-mail: [email protected]

Sonia Anoro Departamento de Química Orgánica, ICMA, Facultad de Ciencias, Universidad de Zaragoza, E-50009, Aragon, Spain Fax: E-mail: [email protected]

Santiago Franco Departamento de Química Orgánica, ICMA, Facultad de Ciencias, Universidad de Zaragoza, E-50009, Aragon, Spain Fax: E-mail: [email protected]

Jose M. Gascon Departamento de Química Orgánica, ICMA, Facultad de Ciencias, Universidad de Zaragoza, E-50009, Aragon, Spain Fax: E-mail: [email protected]

Victor Martin Departamento de Química Orgánica, ICMA, Facultad de Ciencias, Universidad de Zaragoza, E-50009, Aragon, Spain Fax: E-mail: [email protected]

Francisco L. Merchan Departamento de Química Orgánica, ICMA, Facultad de Ciencias, Universidad de Zaragoza, E-50009, Aragon, Spain Fax: E-mail: [email protected]

Julia Revuelta Departamento de Química Orgánica, ICMA, Facultad de Ciencias, Universidad de Zaragoza, E-50009, Aragon, Spain Fax: E-mail: [email protected]

Tomas Tejero Departamento de Química Orgánica, ICMA, Facultad de Ciencias, Universidad de Zaragoza, E-50009, Aragon, Spain Fax: E-mail: [email protected]

Victoria Tuñon Departamento de Química Orgánica, ICMA, Facultad de Ciencias, Universidad de Zaragoza, E-50009, Aragon, Spain Fax: E-mail: [email protected]

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Abstract

An examination of the vinylation of several nitrones is presented. Whereas a complete diastereofacial discrimination was observed upon the addition of vinyl organometallic reagents to α-alkoxy nitrones, the same reaction with α-amino nitrones gave syn adducts in all cases, with the only exception of a L-serine-derived α-amino monoprotected nitrone. The obtained allyl hydroxylamines were easily transformed into synthetically valuable allyl amines.

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A General Method for the Vinylation of Nitrones. Synthesis of Allyl Hydroxylamines and Allyl Amines

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A General Method for the Vinylation of Nitrones. Synthesis of Allyl Hydroxylamines and Allyl Amines

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