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.
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