6533b86efe1ef96bd12cc6e9

RESEARCH PRODUCT

ChemInform Abstract: Stereoselective Synthesis of α-Arylalkylamines by Glycosylation-Induced Asymmetric Addition of Organometallic Compounds to Imines.

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Arylalkylamines are of interest as building blocks for the synthesis of biologically active compounds and as chiral ligands or chiral auxiliaries in stereoselective syntheses [1]. Their stereoselective synthesis has been achieved by enantioselective reduction of ketimines using chiral reagents [2], as for example Corey’s oxaborolidines [3], or proline-derived triacyloxyborohydrides [4]. Particularly efficient asymmetric syntheses of chiral arylalkylamines have been accomplished by Noyori et al. [5] through enantioselective catalysis of hydrogen transfer reactions using a chiral 1,2-diphenyl-ethylenediamine ruthenium catalyst. Enantioselective transferhydrogenationshave also been achieved using a chiral titanocene catalyst [6] or sterically demanding BINOL phosphates [7]. Asymmetric hydrogenation of imines using transition metal catalysts has successfully been used to produce chiral branched amines [8, 9]. An alternative to these reductive procedures consists of the stereoselective addition of organometallic compounds to aldimines [10, 11]. We here report on a new asymmetric addition of organometallic reagents to imines, which is based on the principle of glycosylation-induced asymmetric synthesis [12].