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Updated: Feb 23, 2026

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
Published on: November 23, 2016
Influence of Sulfur on Acid-Mediated Enamide Formation
Joshua A Lutz1, Visal Subasinghege Don1, Revati Kumar1
1Department of Chemistry, Louisiana State University , Baton Rouge, Louisiana 70803, United States.
Abstract:
The acid-mediated condensation of acetamide with butanal dimethylacetal and EtSCH2CH(OMe)2, followed by dehydration, was investigated by electronic structure calculations that supported the prediction that the Z-geometry would be favored in the product. The reaction was investigated experimentally using suitably functionalized cysteine building blocks. Some side reactions and optimization of reaction conditions are reported, en route to identifying a mild, inexpensive Lewis acid that achieves a reasonable yield of (Z)-thioenamide 21 with high stereoselectivity.
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