Issue 88, 2023

Brønsted acid-catalyzed annulation reaction of hydroxamic acids: synthesis of cyclopentane-fused isoxazolidines and their benzilic amide rearrangement

Abstract

Readily available hydroxamic acids were leveraged to access challenging nitrones in the presence of H3PO4 as a Brønsted acid catalyst and engaged in an intramolecular (3+2) annulation reaction to make valuable cyclopentane-fused isoxazolidines with high yields and excellent diastereoselectivity. The products were further utilized in a unique base-promoted benzilic amide rearrangement to provide cyclopentane-fused γ-lactams bearing three contiguous stereocenters as a single diastereomer.

Graphical abstract: Brønsted acid-catalyzed annulation reaction of hydroxamic acids: synthesis of cyclopentane-fused isoxazolidines and their benzilic amide rearrangement

Supplementary files

Article information

Article type
Communication
Submitted
06 Aug 2023
Accepted
10 Oct 2023
First published
11 Oct 2023

Chem. Commun., 2023,59, 13211-13214

Brønsted acid-catalyzed annulation reaction of hydroxamic acids: synthesis of cyclopentane-fused isoxazolidines and their benzilic amide rearrangement

S. L. Mondal, V. Bhajammanavar, I. Ramakrishna and M. Baidya, Chem. Commun., 2023, 59, 13211 DOI: 10.1039/D3CC03810F

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