Catalytic Asymmetric [3 + 2] Annulation via Indolyl Copper–Allenylidene Intermediates: Diastereo- and Enantioselective Assembly of Pyrrolo[1,2-<i>a</i>]indoles
Jian Zhang, Tao Ni, Wu‐Lin Yang, Wei‐Ping Deng
Abstract
A catalytic asymmetric decarboxylative [3 + 2] annulation via indolyl copper–allenylidene amphiphilic intermediates has been developed. This protocol offers a straightforward method for the synthesis of biologically important pyrrolo[1,2-a]indoles bearing contiguous quaternary and tertiary stereogenic centers with excellent diastereo- and enantioselectivities (up to >20:1 dr and >99% ee). In addition, the diversity-oriented synthesis of pyrrolo[1,2-a]indoles was achieved via versatile transformations of the alkyne-containing cycloadducts.
Topics & Concepts
AnnulationChemistryEnantioselective synthesisCatalysisCopperCombinatorial chemistryOrganic chemistryStereochemistryMedicinal chemistryAsymmetric Synthesis and CatalysisAxial and Atropisomeric Chirality SynthesisCatalytic C–H Functionalization Methods