Enantiodivergent RhIII-catalyzed synthesis of imidazo[1,5-a]indole
Marimuthu Bakkiyaraj1, Pazhamalai Anbarasan1
1Department of Chemistry, Indian Institute of Technology Madras, Chennai - 600036, India. anbarasansp@iitm.ac.in.
Abstract:
A general and efficient [4+1]-annulation of indole-N-carboxamide with cyclopropene has been accomplished in the presence of a chiral cyclopentadienyl rhodium catalyst for the synthesis of imidazo[1,5-a]indole. Introduction of one bulky substituent in the chiral cyclopentadienyl ligand without altering the chirality of the binaphthyl fragment reverses the enantioselectivity of the catalytic reaction. Important features of the method include ligand-controlled enantiodivergence, a base-free and redox-neutral approach, synthetic application, and isolation of the potential intermediate.
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