Ethyl N-(diphenylmethylene)glycinate as anionic glycine equivalent. Monoalkylation, dialkylation and michael additions under solid-liquid phase-transfer catalysis

Article abstract of DOI:10.1016/0040-4020(96)00395-X

Ethyl N-(diphenylmethylene)glycinate, 1, undergoes monoalkylations, dialkylations and Michael additions to ethylenic and acetylenic acceptors under appropriate solid-liquid phase transfer catalysis conditions. Further transformations of the α-disubstituted ketimines lead to α-alkylated aspartic and glutamic acid derivatives 10, 15, 19 and 26, to bicyclic amino acids or derivatives featuring pyrazolone and isoxazolone moieties 30 and 33, and to α-substituted (E)-3,4-dehydroglutamic acids. Copyright