40023-41-4Relevant academic research and scientific papers
Enzymatic Synthesis of Amides with Two Chiral Centres
Brieva, Rosario,Rebolledo, Francisca,Gotor, Vincente
, p. 1386 - 1387 (1990)
Candida cylindracea lipase and subtilisin protease were utilised in the enantioselective aminolysis of ethyl (+/-)-2-chloropropionate with racemic amines.
Investigation of the synthetic and mechanistic aspects of the highly stereoselective transformation of α-thioamides to α-thio-β- chloroacrylamides
Murphy, Maureen,Lynch, Denis,Schaeffer, Marcel,Kissane, Marie,Chopra, Jay,O'Brien, Elisabeth,Ford, Alan,Ferguson, George,Maguire, Anita R.
, p. 1228 - 1241 (2008/02/03)
Treatment of a series of α-thioamides with N-chlorosuccinimide results in efficient transformation to the analogous α-thio-β- chloroacrylamides. The mechanistic pathway has been established through isolation and characterisation of intermediate compounds. The scope of the transformation has been explored - aryl and alkylthio substituents, primary, secondary and tertiary amides can be employed. In most instances, the chloroacrylamides are formed exclusively as the Z-stereoisomer; however, with tertiary propanamides or with amides derived from butanoic or pentanoic acid a mixture of E- and Z-stereoisomers is formed. The Royal Society of Chemistry.
