A shorter path: A highly enantioselective bromocyclization of tryptamine has been developed using an anionic chiral phase-transfer catalyst. This method provides a direct approach for preparing chiral 3-bromopyrroloindoline from tryptamine, which enables a four-step enantioselective synthesis of (-)-chimonanthine. PG=protecting group.

Highly asymmetric bromocyclization of tryptophol by using chiral anionic phase-transfer catalyst and DABCO-derived brominating reagent is described. Optimization of the reaction conditions revealed that the reaction rate was accelerated together with improvement of enantioselectivity by addition of catalytic DABCO-derived brominating reagent. From tryptophol, 3-bromofuroindoline could be directly obtained in excellent enantioselectivities by employing this novel methodology.

Enantioselective 3-exo iodo-cycloetherification of allyl alcohols was realized by employing a novel ion-pair organocatalyst.

Interception of Criegee intermediate via tandem acetalization and fragmentation reaction provides a novel oxidative decarbonylation of malondialdehyde.

Abkürzung: Eine enantioselektive Bromcyclisierung von Tryptamin unter Verwendung eines anionischen chiralen Phasentransferkatalysators führt direkt zu chiralen 3‐Brompyrroloindolinen. Die Reaktion ermöglicht eine vierstufige enantioselektive Synthese von (−)‐Chimonanthin. PG=Schutzgruppe.