Chiral C2-symmetric 2,3-disubstituted 1,4-diazabicyclo[2.2.2]octanes (DABCOs) (1) have been utilized as catalysts for asymmetric Baylis-Hillman reactions. Optically active α-methylene-β-hydroxyalkanone was obtained in up to 47% ee. Under high pressure conditions, a remarkable enhancement of both reaction rate and enantioselectivity has been observed.
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