Enantioselective [6 + 2]-Cycloaddition of Transient 3-Methide-3<i>H</i>-pyrroles with 2-Vinylindoles under Chiral Brønsted Acid Catalysis
Rahul Sarkar, Isa Kallweit, Christoph Schneider
Abstract
An organocatalytic, highly diastereo- and enantioselective [6 + 2]-cycloaddition of 3-methide-3H-pyrroles with 2-vinylindoles has been developed. This BINOL phosphoric acid-catalyzed reaction utilizes pyrrole-3-carbinols as precursors for the in situ generation of 3-methide-3H-pyrroles to access densely substituted cyclopenta[b]pyrroles bearing three contiguous stereogenic centers as single diastereomers in good yields with excellent enantioselectivity.
Topics & Concepts
StereocenterChemistryEnantioselective synthesisDiastereomerBrønsted–Lowry acid–base theoryCycloadditionCatalysisOrganocatalysisPhosphoric acidPyrroleStereochemistryMedicinal chemistryOrganic chemistryCombinatorial chemistrySynthesis of Indole DerivativesOrganic Chemistry Cycloaddition ReactionsSynthesis and Characterization of Pyrroles