Enantioselective Synthesis of 5,6-Dihydroindolizines by N-Heterocyclic Carbene (NHC)-Catalyzed Core-Structure-Inspired Strategy of Azolium-Enolate Cascade

Ghosh, A and Shee, S and Barik, S and Gonnade, RG and Biju, AT (2021) Enantioselective Synthesis of 5,6-Dihydroindolizines by N-Heterocyclic Carbene (NHC)-Catalyzed Core-Structure-Inspired Strategy of Azolium-Enolate Cascade. In: Organic Letters .

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Abstract

The core-structure motivated design has allowed the enantioselective synthesis of 5,6-dihydroindolizines via N-heterocyclic carbene (NHC) catalysis. The NHC-catalyzed reaction of α,β-unsaturated aldehydes with the suitably substituted pyrrole derivatives proceed via the initial generation of α,β-unsaturated acylazoliums from enals, and enolates from pyrroles and the reaction culminated in an efficient cascade process involving the Michael-aldol-lactonization-decarboxylation sequence to afford the products in reasonable yields and high selectivities. The method is further extended to the construction of spirocyclic 5,6-dihydroindolizines. © 2021 American Chemical Society.

Item Type:	Journal Article
Publication:	Organic Letters
Publisher:	American Chemical Society
Additional Information:	The copyright for this article belongs to American Chemical Society
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	18 Oct 2021 09:57
Last Modified:	18 Oct 2021 09:57
URI:	http://eprints.iisc.ac.in/id/eprint/69693

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