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Synthesis 2010(19): 3263-3267
DOI: 10.1055/s-0030-1258210
DOI: 10.1055/s-0030-1258210
SPECIALTOPIC
© Georg Thieme Verlag
Stuttgart ˙ New YorkHighly Enantioselective Synthesis of (Diarylmethyl)amines by Rhodium-Catalyzed Arylation of N-Nosylimines Using a Chiral Bicyclo[3.3.0]diene Ligand
Weitere Informationen
Received
7 May 2010
Publikationsdatum:
13. August 2010 (online)
Publikationsverlauf
Publikationsdatum:
13. August 2010 (online)

Abstract
A highly efficient asymmetric arylation of N-nosylimines with arylboronic acids catalyzed by a rhodium-diene complex is described. A wide range of enantiopure (98-99% ee) N-(diarylmethyl)nosylamides, as well as (3S)-2-(4-nosyl)-3-phenylisoindolin-1-one, were obtained in high yields (83-99%) under very mild conditions.
Key words
asymmetric catalysis - amines - arylations - rhodium - diarylmethylamines
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References
The conditions required for the reductive removal of a tosyl group from nitrogen, such as Li/NH3 or SmI2/HMPA/refuxing THF, are incompatible with electron-accepting functional groups, e.g. carbonyl, nitro, or halo; see refs. 6, 7g, and 8a.