An Asymmetric Organocatalytic Quadruple Cascade to Tetraaryl-Substituted 2-Azabicyclo[3.3.0]octadienones

Abstract

A new asymmetric organocatalytic three-component quadruple cascade of α-ketoamides with α,β-unsaturated aldehydes is described. The reaction is catalyzed by the (S)-diphenylprolinol TMS ether catalyst and proceeds via an aza-Michael/aldol condensation/vinylogous Michael/aldol condensation sequence to yield tetraaryl-substituted 2-azabicyclo[3.3.0]octadienone derivatives. The cascade products are obtained with good to very good yields (34–71%), virtually complete diastereoselectivities (>20:1), and very good enantioselectivities (84–97%).

Key words

organocatalysis - domino reactions - quadruple cascade - aza-Michael addition - vinylogous Michael addition

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