Issue 18, 2024

Rh-catalyzed asymmetric allylation of tert-butanesulfinamide

Abstract

Chiral allylic tert-butanesulfinamides were developed as bidentate sulfur–olefin ligands for rhodium. The synthesis of such ligands is normally based on diastereoselective addition or reduction. The preparation of the diastereomer of allylic tert-butanesulfinamides is underdeveloped and the influence of the second chiral center is not fully examined. We report the Rh-catalyzed asymmetric allylation of tert-butanesulfinamides to synthesize all four stereoisomers of allylic tert-butanesulfinamides. The application of the cyclohexyl-substituted bisoxazolinephosphine ligand is the key to control the regioselectivity.

Graphical abstract: Rh-catalyzed asymmetric allylation of tert-butanesulfinamide

Supplementary files

Article information

Article type
Research Article
Submitted
01 Jun 2024
Accepted
15 Jul 2024
First published
16 Jul 2024

Org. Chem. Front., 2024,11, 5093-5098

Rh-catalyzed asymmetric allylation of tert-butanesulfinamide

M. Liu and C. Li, Org. Chem. Front., 2024, 11, 5093 DOI: 10.1039/D4QO00986J

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