A strategy to create the –CH(NR2)CO- moiety from captodative formyl enamines was successfully applied to the synthesis of tertiary α-amino esters.
一种将–CH(NR2)CO-基团从捕获稳定的形式亚胺成功应用于合成三级α-氨基酯的策略。
Transformations des énamines α-formylées: synthèse d’α-amino esters N,N-disubstitués
作者:Alexander Yu. Rulev、Lyudmila I. Larina、Mikhail G. Voronkov
DOI:10.1016/s0040-4039(00)01838-4
日期:2000.12
2-Dialkylaminoalkanoic esters are prepared in moderate yield by the reaction of N,N-disubstituted 2-amino-2-alkenals with dialkylphosphonates in the presence of sodium alcoxide. A mechanism involving an α-keto-β-aminophosphonate as an intermediate is proposed.
alpha-Acylenamines with terminal double bond CH2=CH(NR2)COMe add dialkyl hydrogen phosphites to form only the Michaelis adducts. Contrary to that hydrophosphorylation of a-formylated enamines proceeds regiospecifically at C=O bond. Subsequent isomerization of the products of 1,2-addition and the cleavage of P-C bond of the intermediate alpha-keto-beta-aminophosphonate yields N, N-disubstituted alpha-aminocarboxylates.
KOSKINEN, A.;LOUNASMAA, M., TETRAHEDRON, 1983, 39, N 9, 1627-1633
作者:KOSKINEN, A.、LOUNASMAA, M.
DOI:——
日期:——
Regiospecific functionalisation of carbon atoms α to heterocyclic nitrogen