Rhodium‐Catalyzed Stereoselective Amination of Thioethers with  N ‐Mesyloxycarbamates: DMAP and Bis(DMAP)CH 2 Cl 2  as Key Additives | Zendy

Lebel Hélène | Zendy; Piras Henri | Zendy; Bartholoméüs Johan | Zendy

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Rhodium‐Catalyzed Stereoselective Amination of Thioethers with N ‐Mesyloxycarbamates: DMAP and Bis(DMAP)CH 2 Cl 2 as Key Additives

Author(s) -

Lebel Hélène,

Piras Henri,

Bartholoméüs Johan

Publication year - 2014

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201402961

Subject(s) - chemistry , amination , stereoselectivity , diastereomer , rhodium , catalysis , selectivity , medicinal chemistry , intermolecular force , organic chemistry , molecule

A stereoselective Rh‐catalyzed intermolecular amination of thioethers using a readily available chiral N ‐mesyloxycarbamate to produce sulfilimines in excellent yields and diastereomeric ratio is described. A catalytic mixture of 4‐dimethylaminopyridine (DMAP) and bis(DMAP)CH 2 Cl 2 proved pivotal in achieving high selectivity. The X‐ray crystal structure of the (DMAP) 2 ⋅[Rh 2 {( S )‐nttl} 4 ] complex was obtained and mechanistic studies suggested a Rh II ‐Rh III complex as the catalytically active species.

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