Influence of sulfur on acid-mediated enamide formation
© 2017 American Chemical Society. 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.
Publication Source (Journal or Book title)
Lutz, J., Don, V., Kumar, R., & Taylor, C. (2017). Influence of sulfur on acid-mediated enamide formation. Organic Letters, 19 (19), 5146-5149. https://doi.org/10.1021/acs.orglett.7b02432