Flexible synthesis of pyrimidines with chiral monofluorinated and difluoromethyl side chains.
Chiral pyrimidines with a fluorine atom in the benzylic position are easily accessible in high enantiomeric excesses from optically active propargylic intermediates by two complementary routes. Both the use of optically active propargylic fluorides and the fluorination of the chiral pyrimidine in the final stage give excellent results in terms of enantiocontrol. On the other hand, original pyrimidines with a difluoromethyl side chain are also obtained in a few steps from new propargylic ketones bearing a CHF(2) substituent on the triple bond.
Bannwarth
Pierre
P
Laboratoire de Chimie et Photonique Moléculaires, Université de Rennes 1, CNRS UMR 6510, France.
Valleix
Alain
A
Grée
Danielle
D
Grée
René
R
D000480:Alkynes / Q000737:chemistry; D001969:Bromobenzenes / Q000138:chemical synthesis / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D011743:Pyrimidines / Q000138:chemical synthesis*
D000480:Alkynes; D001969:Bromobenzenes; D006845:Hydrocarbons, Fluorinated; D007659:Ketones; D011743:Pyrimidines