Author/Authors :
Keeling، نويسنده , , Steven P. and Campbell، نويسنده , , Ian B. and Coe، نويسنده , , Diane M. and Cooper، نويسنده , , Tony W.J. and Hardy، نويسنده , , George W. and Jack، نويسنده , , Torquil I. and Jones، نويسنده , , Haydn T. and Needham، نويسنده , , Deborah and Shipley، نويسنده , , Tracy J. and Skone، نويسنده , , Philip A. and Sutton، نويسنده , , Peter W. and Weingarten، نويسنده , , Gordon A. an، نويسنده ,
Abstract :
The efficient synthesis of an α-trifluoromethyl-α-tosyloxymethyl epoxide is reported. This highly versatile building block may be reacted sequentially with two different nucleophiles to furnish α-trifluoromethyl tertiary alcohols. Furthermore, the two enantiomers of this key intermediate have been separated using chiral HPLC and the stereochemistry shown to be conserved during subsequent chemical manipulations. Finally, an enzyme-driven desymmetrisation approach has been successfully employed to confer chirality on an intermediate in the sequence.
Keywords :
Doubly electrophilic , desymmetrisation , Glucocorticoid receptor agonists , ?-Trifluoromethyl epoxide
