171520-75-5Relevant academic research and scientific papers
Domino 1,3-dipolar cycloadditions of n- alkyl-α-amino esters with paraformaldehyde: A direct access to α-hydroxymethyl α-amino acids
Castelló, Luis M.,Nájera, Carmen,Sansano, José M.
, p. 967 - 971 (2014)
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 azomethA?ine 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. Georg Thieme Verlag Stuttgart · New York.
Reactivity of the carbonyl group in water. Generation of azomethine ylides from aqueous formaldehyde: Michael addition versus dipolar trapping
Lubineau, Andre,Bouchain, Giliane,Queneau, Yves
, p. 2433 - 2438 (2007/10/02)
The ability of aqueous formaldehyde to generate azomethine ylides has been studied.Treatment of methyl N-methylglycinate with dipolarophiles in commercial aqueous formaldehyde gives pyrrolidines by azomethine ylide cycloaddition which competes with a Michael addition.
