Issue 5, 2024

Facile synthesis of N-(α-furanyl) alkyl sulfoximines via gold catalyzed Michael addition/cyclization of enynones and sulfoximines

Abstract

Herein, we prepare a new array of N-(α-furanyl) alkyl sulfoximines via a gold catalyzed reaction of enynone with sulfoximine in moderate to very good yields. The reaction involves Michael addition of sulfoximine to enynone, followed by intramolecular cyclization. The presence of two chiral centres led to the formation of a mixture of diastereomers approximately in a 1 : 1 ratio. The salient features of the protocol include broad substrate scope, high efficiency and high yields. The synthetic utility of the protocol is explored using Suzuki–Miyaura cross-coupling and mild, metal-free opening of the furan ring.

Graphical abstract: Facile synthesis of N-(α-furanyl) alkyl sulfoximines via gold catalyzed Michael addition/cyclization of enynones and sulfoximines

Supplementary files

Article information

Article type
Communication
Submitted
07 Oct 2023
Accepted
16 Dec 2023
First published
19 Dec 2023

Org. Biomol. Chem., 2024,22, 945-949

Facile synthesis of N-(α-furanyl) alkyl sulfoximines via gold catalyzed Michael addition/cyclization of enynones and sulfoximines

A. Antony Haritha Mercy, V. R. Padma Priya, R. Hariprasad, K. Gayathri, S. Ravindra, G. Chandra Nandi and R. Kataria, Org. Biomol. Chem., 2024, 22, 945 DOI: 10.1039/D3OB01631E

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