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Updated: Jul 12, 2026

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
Published on: November 23, 2016
Stereoselective intramolecular [4 + 3] cycloadditions of nitrogen-stabilized chiral oxyallyl cations via epoxidation
Hui Xiong1, Jian Huang, Sunil K Ghosh
1Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.
Abstract:
The first intramolecular [4 + 3] cycloaddition reaction using nitrogen-stabilized chiral oxyallyl cations that are tethered to furan or diene through the nitrogen atom is described here. Formation of these nitrogen-stabilized chiral oxyallyl cations is achieved by a chemoselective epoxidation of chiral allenamides via syringe pump addition of dimethyl dioxirane. The ensuing cycloaddition can be carried out with a range of different lengths for the tether, and high diastereoselectivities can be obtained when using chiral allenamides with shorter tethers.
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