Synthesis 2014; 46(07): 967-971
DOI: 10.1055/s-0033-1340816
paper
© Georg Thieme Verlag Stuttgart · New York

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
› Author Affiliations
Further Information

Publication History

Received: 04 December 2013

Accepted after revision: 22 January 2014

Publication Date:
11 February 2014 (eFirst)

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.

Supporting Information

 
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