Abstract
The deprotonation of N-diphenylmethylene-glycine esters, obtained from glycine ester hydrochlorides and benzophenone imine, and reaction of the resulting carbanions with iodomethyl triorganostannanes gives the 3-triorganostannyl-N-diphenylmethylene-alanine esters Me2RSnCH2CH(N=CPh2)COOR′ (1a - e; R = Me, tBu; R′ = Me, Et, tBu, Bz). These title compounds are transformed into their tin monochlorides MeR(Cl)SnCH2CH(N=CPh2)COOR′ (2a - e) by a redistribution reaction with Me2SnCl2. IR and NMR data and the crystal structure of Me2(Cl)SnCH2CH(N=CPh2)COOEt (2b) reveal for 2a - e an intramolecular coordination of the ester C = 0 group at the tin atom. Mild two-phase hydrolysis of 1a - e with 1N HCl gives the 3-triorganostannyl-alanine ester hydrochlorides Me2RSnCH2CH(NH2)COOR′ · HCl (3a - e). The transformation of 3a - e into the corresponding alanine esters Me2RSnCH2CH(NH2)COOR′ (4a - e) could be realized with NH3 in chloroform. 4a - e are of limited thermal stability.
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