N-monochlorination of N-unprotected alpha-amino esters and alpha-amino-beta-diesters was efficiently and very simply effected by using inexpensive effervescent sodium dichloroisocyanurate tablets for water disinfection in a biphasic organic solvent-water system. Subsequent dehydrochlorination provided alpha,beta-didehydroaminoacid esters, whose hydrogenation would allow the starting compounds to be easily racemized.
A highly efficient method for the alpha,beta-dehydrogenation of alpha-amino esters and alpha-amino-beta-diesters / M. Pallavicini, C. Bolchi, L. Fumagalli, O. Piccolo, E. Valoti. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 51:42(2010), pp. 5540-5542. [10.1016/j.tetlet.2010.08.006]
A highly efficient method for the alpha,beta-dehydrogenation of alpha-amino esters and alpha-amino-beta-diesters
M. Pallavicini;C. Bolchi;L. Fumagalli;E. Valoti
2010
Abstract
N-monochlorination of N-unprotected alpha-amino esters and alpha-amino-beta-diesters was efficiently and very simply effected by using inexpensive effervescent sodium dichloroisocyanurate tablets for water disinfection in a biphasic organic solvent-water system. Subsequent dehydrochlorination provided alpha,beta-didehydroaminoacid esters, whose hydrogenation would allow the starting compounds to be easily racemized.
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