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Phosphine-Catalyzed Stereoselective Tandem Annulation Reaction for the Synthesis of Chromeno[4,3-<i>b</i>]pyrroles

Zonghao Dai, Jin Zhu, Wenbo Su, Wuxian Zeng, Ziqi Liu, Ming Chen, Qingfa Zhou

2020Organic Letters39 citationsDOI

Abstract

A phosphine-catalyzed tandem cyclization reaction has been developed to provide a series of chromeno[4,3-b]pyrrole derivatives, which contain three consecutive asymmetric centers. The reaction has a good yield, excellent stereoselectivity, and Z/E selectivity. The new method is simple, requires only mild conditions, and shows tolerance for various functional groups. Similarly, this reaction can be catalyzed by a chiral phosphine catalyst to achieve asymmetric synthesis.

Topics & Concepts

ChemistryStereoselectivityAnnulationPhosphineTandemYield (engineering)CatalysisPyrroleCombinatorial chemistrySelectivityReaction conditionsCascade reactionMedicinal chemistryOrganic chemistryMaterials scienceComposite materialMetallurgyCarbohydrate Chemistry and SynthesisOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization Methods