Stereoselective rhodium-catalyzed lmination of sulfides

Organic Letters

Volumn 10, Issue 23, 2008, Pages 5473-5476

  Collet, Florence ^a   Dodd, Robert H ^a   Dauban, Philippe ^a  

^a INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

IMINE; RHODIUM; SULFIDE;

ARTICLE; CATALYSIS; CHEMISTRY; ENZYME SPECIFICITY; STEREOISOMERISM;

CATALYSIS; IMINES; RHODIUM; STEREOISOMERISM; SUBSTRATE SPECIFICITY; SULFIDES;

EID: 61349127170     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802295b     Document Type: Article

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70. 4] afforded compound 4a in 90% yield but with a lower de of 62%. The p-nitro analog of 4a was isolated in 76% yield and 70% de starting from N-(p-toluenesulfonyl)-p- nitrobenzenesulfonimidamide. Finally, use of the less soluble PhI=O led to a decrease of the reactivity and the selectivity (69% yield and 60% de).
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74. It should be mentioned that this procedure cannot be applied to sulfilimines of type 4 because use of magnesium in methanol under sonication leads to the starting sulfide 3.