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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.

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Authors

Priscilla Mendon�a Matos

William Lewis

Profile image of ROBERT STOCKMAN

ROBERT STOCKMAN robert.stockman@nottingham.ac.uk
Professor of Organic Chemistry



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

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