Catalytic, Enantioselective C2-Functionalization of 3-Aminobenzofurans Using N-Heterocyclic Carbenes

Barik, S and Shee, S and Ghosh, A and Biju, AT (2020) Catalytic, Enantioselective C2-Functionalization of 3-Aminobenzofurans Using N-Heterocyclic Carbenes. In: Organic Letters, 22 (10). pp. 3865-3869.

	PDF org_let_22-10_3865-3869_2020.pdf - Published Version Restricted to Registered users only Download (1MB) | Request a copy
	PDF ol0c01112_si_001.pdf - Published Supplemental Material Restricted to Registered users only Download (17MB) | Request a copy

Abstract

N-Heterocyclic carbene catalyzed enantioselective functionalization of 3-aminobenzofurans at the C2-position was realized using 2-bromoenals as the coupling partner. The reaction proceeds via generation of chiral α,β-unsaturated acylazoliums and follows an aza-Claisen rearrangement. The initially formed dihydropyridinone undergoes ring-opening catalyzed by Mg to afford the δ-amino acid derivatives. The reaction worked with 3-aminobenzothiophenes as well, and the C2-alkylated products were formed in moderate to high yields and selectivity. © Copyright © 2020 American Chemical Society.

Item Type:	Journal Article
Publication:	Organic Letters
Publisher:	AMER CHEMICAL SOC
Additional Information:	The copyright of this article belongs to AMER CHEMICAL SOC
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	23 Jun 2020 10:10
Last Modified:	23 Jun 2020 10:10
URI:	http://eprints.iisc.ac.in/id/eprint/65513

Actions (login required)

View Item