An effective route to fluorine containing asymmetric alpha-aminophosphonates using chiral Bronsted acid catalyst.
Asymmetric addition of dialkyl phosphites (--CH2CH3, --CH2CH2CH3, --CH(CH3)2, --CH2(CH2)3CH3, --CH2CH2OCH3 and --CH2CH2OC2H5) induced by chiral organocatalyst e.g. (R)- and (S)-3,3'-[3,5-bis(trifluoromethyl)phenyl]2-1,1'-binaphthyl phosphate on fluorinated aldimines derived from cinnamaldehyde has been found effective to give new bioactive alpha-aminophosphonates in good yields (58-73%) and high enantiomeric excess (64.6%-90.6%) under mild conditions.
Bhadury
Pinaki S
PS
Center for Research and Development of Fine Chemicals, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, People's Republic of China.
Zhang
Yuping
Y
Zhang
Sha
S
Song
Baoan
B
Yang
Song
S
Hu
Deyu
D
Chen
Zhuo
Z
Xue
Wei
W
Jin
Linhong
L
D000143:Acids / Q000737:chemistry; D000171:Acrolein / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D002384:Catalysis; D005459:Fluorides / Q000737:chemistry; D005461:Fluorine / Q000737:chemistry*; D007097:Imines / Q000138:chemical synthesis*; D015394:Molecular Structure; D063065:Organophosphonates / Q000737:chemistry*; D017905:Phosphites / Q000737:chemistry; D013816:Thermodynamics
D000143:Acids; D007097:Imines; D063065:Organophosphonates; D017905:Phosphites; D005461:Fluorine; D000171:Acrolein; D005459:Fluorides; C012843:cinnamaldehyde