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The chiral aziridino alcohols 1 - 3 have been prepared either from amino acids (1a from serine; 1b - 1i and 3 from threonine; 2a - 2e from allo-threonine) or via asymmetric synthesis (1j, 1k, 1l and 2f from methyl cinnamate). These easily available ligands act as catalysts for the enantioselective addition of diethylzinc to benzaldehyde, with up to 90% stereoselectivity. The absolute configuration...
The C 2 -symmetric bis(aziridine) ligands 1 - 5 have been screened in the enantioselective addition of organolithium reagents to imines. Ligand 1 (used in stoichiometric amounts) was found to be superior in terms of chemical yield and enantioselectivity, the best result being 90% yield and 89% e.e. in the addition of vinyllithium to imine 6a. Use of ligand 1 in substoichiometric amounts...
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