Screening of a modular sugar-based phosphoroamidite ligand library in the asymmetric nickel-catalyzed trialkylaluminium addition to aldehydes

A modular sugar-based phosphoroamidite ligand library for the Ni-catalyzed trialkylaluminium addition to aldehydes has been synthesized and screened. After systematic variation of the sugar backbone, the substituents at the phosphoroamidite moieties and the flexibility of the ligand backbone, the monophosphoroamidite ligand 3-amine-3-deoxy-1,2:5,6-di-O-isopropylidene-((3,3′-di-trimethylsilyl-1,1′-biphenyl-2,2′-diyl)phosphite)-α-d-glucofuranose 1d were found to be optimal. Activities were high and enantioselectivities were good (ees up to 78%) for several aryl aldehydes.

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