Nitrones are important 1,3-dipoles that endure cycloadditions with alkenes affording versatile isoxazolidine skeletons.1 Frederickson et al. developed Pd(II) catalyzed cyclization-cycloaddition cascade reaction of alkenyl oxime and N-methylmalimide (NMM) affording varied isoxazolidines.2Despite the potential of this technique, no enantioselective version has been reported. Herein, we report the first enantioselective protocol of TfOH-initiated oxime-nitrone-isoxazolidine cascade catalyzed by Pd(II)-phosphine complexes. After screening of different chiral catalytic combinations, Tol-SDP ligand is found to be highly effective in dominating both of enantio- and diastereoselectivities of the product having four contiguous stereogenic centers.

Enantioselective palladium(II) catalyzed cyclization-cycloaddition cascade reactions of alkenyl oximes

248th National Meeting (2014)

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