Organocatalyst-mediated asymmetric one-pot/two domino/three-component coupling reactions for the synthesis of trans -hydrindanes.

Highly substituted trans -hydrindanes were synthesized by the three-component coupling reactions of 1,3-diethyl 2-(2-oxopropylidene)propanedioate and two different α,β-unsaturated aldehydes catalyzed by diphenylprolinol silyl ether. The reaction proceeds via two successive independent catalytic domino reactions in a one-pot reaction by a single chiral catalyst. Domino reactions involve Michael/Michael and Michael/aldol reactions to afford trans -hydrindanes with excellent diastereoselectivity and nearly optically pure form.