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4‐l‐menthyloxycarbonyl 5‐aryl prolinates were studied as organocatalysts of a novel three‐component reaction of cyclohexanone, benzoic acid, and β‐nitrostyrene. The presence of ortho‐halogen atom in 5‐aryl fragment of the catalyst is favored for driving the formation of chiral 7a‐hydroxyoctahydro‐2H‐indol‐2‐one scaffold. 5‐(o‐Chlorophenyl) prolinate selectively afforded 3‐phenyl‐7a‐hydroxyoctahydro‐2...
Tricyclic lactams containing the pyrrolizidin-3-one moiety were synthesized by the three-component reaction of aromatic aldehydes, glutamic acid (or glutamine), and N-methylmaleimide. The cascade reactions involve the stereospecific generation of azomethine ylides, the 1,3-dipolar endo- and exo-cycloaddition of a dipolarophile to the ylides, and the lactamization and afford two series of stereoisomeric...
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