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Title
| - Asymmetric Synthesis of anti- and syn-β-Amino Alcohols byReductive Cross-Coupling of Transition Metal-Coordinated PlanarChiral Arylaldehydes with Aldimines
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Abstract
| - Samarium iodide-mediated cross-coupling of N-tosyl ferrocenylideneamine with planar chiralferrocenecarboxaldehydes or benzaldehyde chromium complexes gave diastereoselectively thecorresponding anti-β-amino alcohol derivatives in good yields, while N-tosyl benzylideneamineproduced syn-β-amino alcohols by coupling with planar chiral arylaldehydes. Dynamic kineticresolution of a configurationally equilibrated reactive species generated from achiral N-tosylferrocenilideneamine and benzylideneamine by reduction with samarium iodide was observed inthe cross-coupling with planar chiral arylaldehydes giving both antipodes of β-amino alcoholsdepending on the planar chirality. The obtained anti-β-amino alcohol with the ferrocene ring wasutilized as a chiral ligand for catalytic asymmetric reduction of acetophenone.
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