Document Type
Article
Department or Administrative Unit
Chemistry
Publication Date
6-11-2020
Abstract
A solvent-controlled protocol for the direct and transition metal-free addition of alkenyl Grignard reagents to vicinally functionalized sp3-rich morpholinones has been developed, leading to the chemo and regioselective synthesis of lactam-bearing homoallylic ketones. The addition of lithium chloride proved to be essential. In cases where a new stereocenter is generated, the doubly branched homoallylic ketones are obtained in unexpectedly high diastereoselectivities. Efforts to extend the methodology to other heterosubstituted lactams revealed some important reactivity and selectivity differences.
Recommended Citation
Farah, A. O., Rabah, M., & Beng, T. K. (2020). Transition metal-free domino acyl substitution/Michael addition of alkenyl Grignard reagents to lactam esters: synthesis of lactam-bearing homoallylic ketones. RSC Advances, 10(38), 22454–22459. https://doi.org/10.1039/d0ra03885g
Journal
RSC Advances
Creative Commons License
This work is licensed under a Creative Commons Attribution-Noncommercial 3.0 License
Rights
© The Royal Society of Chemistry 2020
Comments
This article was originally published Open Access in RSC Advances. The full-text article from the publisher can be found here.