Desymmetrization of Sulfoximines through Enantioselective Remote C−H Borylation Utilizing Iridium – Lewis Acid Bifunctional Catalysis

Sen, Abhirup (2023) Desymmetrization of Sulfoximines through Enantioselective Remote C−H Borylation Utilizing Iridium – Lewis Acid Bifunctional Catalysis. Masters thesis, Indian Institute of Science Education and Research Kolkata.

Text (MS dissertation of Abhirup Sen (18MS006)) Thesis_18MS006.pdf - Submitted Version Restricted to Repository staff only Download (3MB)

Abstract

Creating complex chiral scaffolds from simple compounds has been a long-standing problem in organic synthesis. Recent advances in desymmetrization reactions have opened up new avenues in this context. Considering versatility of organoboron compounds in organic synthesis, the iridium-catalyzed direct C–H bond borylation reaction gained huge attention. Undoubtably, C–H borylation for fostering desymmetrization has garnered much interest. To achieve selectivity, directing group methods and non-covalent interaction have been playing a vital role. However, for obvious reasons, there is a scarcity of strategies which, along with inducing chirality, can impart distal functionalization. Herein, we report a protocol for enantioselective remote C–H borylation of sulfoximines via iridium-Lewis acid bifunctional catalysis. We chose sulfoximines as scientists have recently been exploring ways to incorporate the sulfoximine functional group into various bioactive chemicals and therapeutic molecules due to its distinctive characteristics. As a result, an efficient protocol for harnessing chiral sulfoximines with complex functionality is greatly needed. So far, we have optimized the reaction condition to achieve an enantioselectivity up to 88%. Further investigation and exploration of scope is the outlook of this thesis.

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