Influence of Sulfur on Acid-Mediated Enamide Formation.

Autor: Lutz JA; Department of Chemistry, Louisiana State University , Baton Rouge, Louisiana 70803, United States., Subasinghege Don V; Department of Chemistry, Louisiana State University , Baton Rouge, Louisiana 70803, United States., Kumar R; Department of Chemistry, Louisiana State University , Baton Rouge, Louisiana 70803, United States., Taylor CM; Department of Chemistry, Louisiana State University , Baton Rouge, Louisiana 70803, United States.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2017 Oct 06; Vol. 19 (19), pp. 5146-5149. Date of Electronic Publication: 2017 Sep 11.
DOI: 10.1021/acs.orglett.7b02432
Abstrakt: The acid-mediated condensation of acetamide with butanal dimethylacetal and EtSCH 2 CH(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.
Databáze: MEDLINE
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