Concise synthesis of enantiopure alpha-trifluoromethyl alanines, diamines, and amino alcohols via the Strecker-type reaction.
Diastereomerically pure alpha-trifluoromethyl alpha-amino nitriles obtained by Strecker-type reactions from chiral CF3 imines and iminium proved to be very attractive versatile intermediates for the synthesis of various alpha-trifluoromethyl amino compounds. From these synthons, both enantiomers of alpha-trifluoromethyl alanine, trifluoromethyl 1,2-diamines, and amino alcohols were conveniently obtained in enantiopure form in high yields in a few steps.
Huguenot
Florent
F
Laboratoire Réactions Sélectives et Applications, UMR CNRS 6519, Université de Reims-Champagne-Ardenne, Faculté des Sciences, BP 1039, 51687 Reims Cedex 2, France.
Brigaud
Thierry
T
D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D003959:Diamines / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D007097:Imines / Q000737:chemistry; D013237:Stereoisomerism
D000605:Amino Alcohols; D003959:Diamines; D007097:Imines; C507723:alpha-trifluoromethylalanine; D000409:Alanine