The hydrostannation of a propargylglycine derivative

Article abstract of DOI:10.1016/S0022-328X(96)06752-6

The hydrostannation of methyl (R,S)-2-(N-diphenylmethylidene) aminopent-4-ynoate induced by a wide variety of transition metal complexes has been studied. The resulting isomeric α-amino acid derivatives featured a tributylvinylstannane in the side-chain and were separated by chromatography. A total of 24 different conditions were screened for this reaction in an attempt to effect a regioselective addition of tributyltin hydride to the alkyne group. Regioisomeric mixtures were formed in all cases and for some catalysts reduction to the allylglycine derivative was also significant.