Transition metal-free domino acyl substitution/Michael addition of alkenyl Grignard reagents to lactam esters: synthesis of lactam-bearing homoallylic ketones

Authors

Abdikani Omar Farah, Central Washington University
Muhannad Rabah, Central Washington University
Timothy K. Beng, Central Washington University

Department or Administrative Unit

Chemistry

Document Type

Article

Creative Commons License

This work is licensed under a Creative Commons Attribution-Noncommercial 3.0 License

Author Copyright

© The Royal Society of Chemistry 2020

Publication Date

6-11-2020

Journal

RSC Advances

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.

Comments

This article was originally published Open Access in RSC Advances. The full-text article from the publisher can be found here.

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