Verma Saumya, Singh Vikram, Jat Jawahar L, Tiwari Bhoopendra
Department of Chemistry, Babasaheb Bhimrao Ambedkar University (A Central University) Vidya Vihar, Raebareli Road, Lucknow 226025, Uttar Pradesh, India.
Department of Biological and Synthetic Chemistry, Centre of Biomedical Research, SGPGIMS-Campus, Raebareli Road, Lucknow 226014, India.
J Org Chem. 2024 Jun 7;89(11):8201-8207. doi: 10.1021/acs.joc.3c02478. Epub 2024 May 27.
The Beckmann reaction is one of the most atom-economical methods for the preparation of amides from ketones. Unlike ketones, the multiple competing reactivities of enones as well as the requirement of demanding reaction conditions for in situ generation of oximes have severely impacted the application of this reaction for the preparation of α,β-unsaturated amides. Herein, we describe the first chemoselective method for the direct conversion of enones to the corresponding α,β-unsaturated amides using -Boc--tosylhydroxylamine.
贝克曼反应是由酮制备酰胺最原子经济的方法之一。与酮不同，烯酮的多种竞争反应性以及原位生成肟所需的苛刻反应条件严重影响了该反应在制备α,β-不饱和酰胺中的应用。在此，我们描述了第一种使用-Boc--对甲苯磺酰羟胺将烯酮直接化学选择性转化为相应α,β-不饱和酰胺的方法。
