De novo synthesis of troc-protected amines: Intermolecular rhodium-catalyzed C-H amination with N-tosyloxycarbamates

Organic Letters

Volumn 9, Issue 4, 2007, Pages 639-642

  Lebel, Hélène ^a   Kim, Huard ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE; AMINE; CARBAMIC ACID DERIVATIVE; CARBONIC ACID DERIVATIVE; POTASSIUM; POTASSIUM CARBONATE; RHODIUM; TOLUENESULFONIC ACID DERIVATIVE;

AMINATION; ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKANES; AMINATION; AMINES; CARBAMATES; CARBONATES; CATALYSIS; POTASSIUM; RHODIUM; STEREOISOMERISM; TOSYL COMPOUNDS;

EID: 33847787039     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062953t     Document Type: Article

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36. In spite of that, others have established the feasibility of performing such a reaction even with a single equivalent of starting material: see ref 8 and 9 for details.
37. These N-tosyloxycarbamate reagents have been chosen, as neither contained reactive C-H bonds (entries 1 and 5-8) that could compete via an intramolecular pathway. Furthermore, substrates containing primary C-H bonds or terminal alkenes (which are typically less reactive) were also tested (entries 2-4).
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39. 4 gave 42% yield of amine 4 with a 15:1 ratio.
40. The enantiomeric ratio was measured on the crude material. A purification procedure cannot be used as an argument to explain the enantiomeric enrichment, thus the chiral catalyst must be involved to account for the observed enantioselectivity.
41. 2.