An efficient synthesis of enantiomerically enriched trifluoromethylated 1,2-diols and 1,2-amino alcohols with quaternary stereocenters by diastereoselective addition of TMSCF3 to chiral 2-acyl-1,3-perhydrobenzoxazines.
TMSCF3 adds to chiral 2-acyl-1,3-perhydrobenzoxazines with total diastereoselectivity leading to quaternary trifluoromethyl alcohols. Further transformation of the addition products yields enantiomerically enriched trifluoromethylated 1,2-diols and 1,2-amino alcohols.
Pedrosa
Rafael
R
Departamento de Química Organica, Facultad de Ciencias, Universidad de Valladolid, Dr. Mergelina s/n, 47011-Valladolid, Spain. pedrosa@qo.uva.es
Sayalero
Sonia
S
Vicente
Martina
M
Maestro
Alicia
A
D000605:Amino Alcohols / Q000138:chemical synthesis*; D048588:Benzoxazines / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
D000605:Amino Alcohols; D048588:Benzoxazines; D006845:Hydrocarbons, Fluorinated; D012821:Silanes; C509472:trimethyl(trifluoromethyl)silane