Department of Chemistry
Indian Institute of Technology Madras, Chennai
Research Proposal Seminar
‘’Synthetic Approaches to Indole Based Atropisomeric Compounds’’

Name: Sumran Raikwar (CY20D040) Date: 25-09-2023
Venue: CB 310 (Seminar Hall) Time: 03.00 pm
Abstract: Axial chirality refers to stereoisomerism resulting from the nonplanar arrangement of four groups in pairs about a chiral axis.1 Axially chiral molecules are recognized as unique structural motifs in natural products and biologically active molecules. They are also considered as privileged chiral ligands and catalysts.2,3 Among many structural types like, biaryls, non-biaryls, hetero-Ar based atropisomers, the indole based atropisomeric compounds represent a unique class. Recently, our research group reported the first example of butenolide based atropisomeric compounds, employing the Z-enoate assisted Meyer-Schuster (M-S) rearrangement (developed in our laboratory in 2016 for the interception of an allenol intermediate with nucleophiles).4 In this presentation, I will be discussing a series of indole-based atropisomers and approaches for their synthesis. Under my research proposal, I will be sharing our efforts towards the development of approaches for the synthesis of 2-/3-vinylindole based atropisomeric, and chiral centre induced generation of chiral axis. Scheme: I) Examples of axially chiral indole-based molecules II) Research Proposal Work

Reference: 1) Zhang, Z. X.; Zhai, T. Y.; Ye, L. W. Chem Catal., 2021, 1, 1378. 2) O. Baudoin, F. Gueritte, Stud. Nat. Prod. Chem., 2003, 29, 355. 3) Li, T. Z.; Liu, S.J.; Tan, W.; Shi, F. Chem. Eur. J., 2020, 26, 15779. 4) (a) Tharra, P.; Baire, B. Chem. Commun. 2016, 52, 14290. (b) D. Roy, B. Baire, Chem. Eur. J., 2021, 27, 4009