Domino 1,3-Dipolar Cycloadditions of N-Alkyl-α-Amino Esters with Paraformaldehyde: A Direct Access to α-Hydroxymethyl α-Amino Acids

Luis M. Castelló; Carmen Nájera; José M. Sansano

doi:10.1055/s-0033-1340816

Synthesis, Table of Contents

Synthesis 2014; 46(07): 967-971
DOI: 10.1055/s-0033-1340816

paper

Domino 1,3-Dipolar Cycloadditions of N-Alkyl-α-Amino Esters with Paraformaldehyde: A Direct Access to α-Hydroxymethyl α-Amino Acids

Luis M. Castelló

Departamento de Química Orgánica e Instituto de Síntesis Orgánica (ISO), Facultad de Ciencias, Universidad de Alicante, 03080 Alicante, Spain Fax: +34(96)5903549 Email: cnajera@ua.es Email: jmsansano@ua.es

,

Carmen Nájera*

Departamento de Química Orgánica e Instituto de Síntesis Orgánica (ISO), Facultad de Ciencias, Universidad de Alicante, 03080 Alicante, Spain Fax: +34(96)5903549 Email: cnajera@ua.es Email: jmsansano@ua.es

,

José M. Sansano*

Departamento de Química Orgánica e Instituto de Síntesis Orgánica (ISO), Facultad de Ciencias, Universidad de Alicante, 03080 Alicante, Spain Fax: +34(96)5903549 Email: cnajera@ua.es Email: jmsansano@ua.es

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Abstract

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Abstract

N-Alkyl-α-amino esters undergo a domino reaction, based on the iminium cation generation, with paraformaldehyde, followed by a 1,3-dipolar cycloaddition of the stabilized azomethine ylide with another equivalent of formaldehyde. The resulting products are oxazolidines, which can be transformed after hydrolysis into α-hydroxymethyl α-amino acid or its derivatives. The diastereoselective 1,3-dipolar cycloaddition was performed using sarcosine (–)-menthyl or (–)-8-phenylmenthyl esters affording the cyclic product with moderate enantiomeric ratio.

Key words

cycloaddition - azomethine ylides - paraformaldehyde - serine

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References

References

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Supplementary Material

Supporting Information