General Method for the Asymmetric Synthesis of N–H Sulfoximines via C–S Bond Formation

Mendon�a Matos, Priscilla; Lewis, William; Argent, Stephen P.; Moore, Jonathan C.; Stockman, Robert A.

Abstract

A versatile method for the synthesis of enantioenriched N–H sulfoximines is reported. The approach stems from the organomagnesium-mediated ring opening of novel cyclic sulfonimidate templates. The reactions proceed in high yield and with excellent stereofidelity with alkyl, aryl, and heteroaryl Grignard reagents. The chiral auxiliary is readily removed from the resultant sulfoximines via an unusual oxidative debenzylation protocol that utilizes molecular oxygen as the terminal oxidant. This provides a general strategy for the synthesis of highly enantioenriched N–H sulfoximines.

Citation

Mendonça Matos, P., Lewis, W., Argent, S. P., Moore, J. C., & Stockman, R. A. (in press). General Method for the Asymmetric Synthesis of N–H Sulfoximines via C–S Bond Formation. Organic Letters, 22(7), 2776-2780. https://doi.org/10.1021/acs.orglett.0c00761

• Journal Article Type: Article
• Acceptance Date: Feb 28, 2020
• Online Publication Date: Mar 16, 2020
• Deposit Date: May 1, 2020
• Publicly Available Date: Mar 17, 2021
• Journal: Organic Letters
• Print ISSN: 1523-7060
• Electronic ISSN: 1523-7052
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 22
• Issue: 7
• Pages: 2776-2780
• DOI: https://doi.org/10.1021/acs.orglett.0c00761
• Keywords: Physical and Theoretical Chemistry; Organic Chemistry; Biochemistry
• Public URL: https://nottingham-repository.worktribe.com/output/4175826
• Publisher URL: https://pubs.acs.org/doi/10.1021/acs.orglett.0c00761