Cerium(IV) sulfate catalyzed one-pot three-component diastereo selective synthesis of 4-amidotetrahydropyrans

Author： Selvam Nagarajan P.   Perumal Paramasivan T.  

Publisher： NRC Research Press

ISSN： 1480-3291

Source： Canadian Journal of Chemistry, Vol.87, Iss.6, 2009-06, pp. : 698-705

Disclaimer: Any content in publications that violate the sovereignty, the constitution or regulations of the PRC is not accepted or approved by CNPIEC.

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Abstract

A convenient and diastereoselective one-pot synthesis of cis-4-amidotetrahydropyrans is described. This simple protocol involves Prins cyclization of homoallylic alcohol and aldehydes, followed by Ritter reaction of acetonitrile leading to the formation of cis-4-acetamidopyrans in good yields.On décrit une méthode de synthèse monotope commode et diastéréosélective des cis-4-amidotétrahydropyranes. Ce protocole simple implique des réactions de cyclisation de Prins entre l’alcool homoallylique et divers aldéhydes, suivies d’une réaction de Ritter avec de l’acétonitrile qui conduit à la formation des cis-4-acétamidopyranes avec de bons rendements.

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