TY - JOUR AU - Castelló, Luis M.; Nájera, Carmen; Sansano, José M. TI - Domino 1,3-Dipolar Cycloadditions of N-Alkyl-α-Amino Esters with Paraformaldehyde: A Direct Access to α-Hydroxymethyl α-Amino Acids SN - 0039-7881 SN - 1437-210X PY - 2014 JO - Synthesis JF - Synthesis LA - EN VL - 46 IS - 07 SP - 967 EP - 971 ET - 2014/02/11 DA - 2014/03/20 KW - cycloaddition KW - azomethine ylides KW - paraformaldehyde KW - serine AB - 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. PB - © Georg Thieme Verlag DO - 10.1055/s-0033-1340816 UR - http://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-0033-1340816 ER -