An enantioselective synthetic method for the preparation of 1,8-dihydroindeno[2,1-b]pyrroles that relies on the chiral Brønsted acid- and gold(I)-catalyzed dehydrative Nazarov-type electrocyclization (DNE)/hydroamination of electron-rich β-amino-1,4-enyols is described. Achieved in product yields up to 99% and enantiomeric excess (ee) values up to 99%, the asymmetric reaction provides access to a novel class of compounds containing both the privileged 1H-indene and pyrrole scaffold, which may lead to novel pharmacological applications. (Figure presented.).
- asymmetric synthesis
- chiral Brønsted acid catalysis
- dehydrative Nazarov-type electrocyclization
- gold catalysis
- N-heterocyclic synthesis