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An Efficient Method for the Synthesis of Enantiopure Phosphine—Imidazoline Ligands: Application to the Ir-Catalyzed Hydrogenation of Imines.

✍ Scribed by Ester Guiu; Carmen Claver; Jordi Benet-Buchholz; Sergio Castillon

Publisher: John Wiley and Sons
Year: 2005
Weight: 29 KB
Volume: 36
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.200511062

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✦ Synopsis

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An Efficient Method for the Synthesis of Enantiopure Phosphine-Imidazoline Ligands: Application to the Ir-Catalyzed Hydrogenation of Imines. -Novel arylimidazolines (I), obtained efficiently via reaction of aryldithioesters with chiral diamines, are used as ligands in the asymmetric iridium-catalyzed hydrogenation of imines to amines. Although excellent conversions are achieved, the enantioselectivity is only low to moderate and cannot be improved by use of various additives like Bu 4 NI, phthalimide or iodine. The electronic properties of the imidazolines (I), however, can be influenced by the N-substituent, which will be an interesting subject of further studies.

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