99209-06-0Relevant academic research and scientific papers
Amino Acids, 4 - Enantioselective Synthesis of N-Substituted α-Amino Carboxylic Acids from α-Hydroxy Carboxylic Acids
Effenberger, Franz,Burkard, Ulrike,Willfahrt, Joachim
, p. 314 - 333 (2007/10/02)
With primary and secondary amines, the (S)-α-(trifluoromethylsulfonyloxy) carboxylates (S)-3 afford in an SN2 reaction the N-substituted (R)-α-amino carboxylates (R)-5, (R)-9, and (R)-12, resp.The rates of α-substituted ethyl propionates decrease in the order of the substituents triflate (3a) >> bromide (8a) > mesylate (7a) >= tosylate (7b) > chloride (8b); in the reactions with amines, decreasing reactivity affords increasing racemisation and elimination as a consequence of the more drastic conditions which are required
