G. Faita, M. Mella, M. Toscanini
Apr 17, 2010
Citations
0
Influential Citations
16
Citations
Journal
Tetrahedron
Abstract
Abstract The asymmetric Friedel–Crafts reaction between methyl ( E )-2-oxo-4-aryl-3-butenoates ( 1a – c ) and activated benzenes ( 2a – d ) has been efficiently catalyzed by the Sc III triflate complex of (4′ S ,5′ S )-2,6-bis[4′-(triisopropylsilyl) oxymethyl-5′-phenyl-1′,3′-oxazolin-2′-yl]pyridine (pybox 3 ). The 4,4-diaryl-2-oxo-butyric acid methyl esters ( 4 ) are usually formed in good yields and the enantioselectivity is up to 99% ee. The sense of the stereoinduction can be rationalized with the same octahedral complex ( 10 ) between 1 , pybox 3 and Sc triflate already proposed for other reactions involving pyruvates, and catalyzed by the same complex.