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Asymmetric Synthesis of anti - and syn -β-Amino Alcohols by Reductive Cross-Coupling of Transition Metal-Coordinated Planar Chiral Arylaldehydes with Aldimines

2002; American Chemical Society; Volume: 67; Issue: 26 Linguagem: Inglês

10.1021/jo0205412

1520-6904

Yoshie Tanaka, Nobukazu Taniguchi, Takayuki Kimura, Motokazu Uemura,

Asymmetric Hydrogenation and Catalysis

Samarium iodide-mediated cross-coupling of N-tosyl ferrocenylideneamine with planar chiral ferrocenecarboxaldehydes or benzaldehyde chromium complexes gave diastereoselectively the corresponding anti-beta-amino alcohol derivatives in good yields, while N-tosyl benzylideneamine produced syn-beta-amino alcohols by coupling with planar chiral arylaldehydes. Dynamic kinetic resolution of a configurationally equilibrated reactive species generated from achiral N-tosyl ferrocenilideneamine and benzylideneamine by reduction with samarium iodide was observed in the cross-coupling with planar chiral arylaldehydes giving both antipodes of beta-amino alcohols depending on the planar chirality. The obtained anti-beta-amino alcohol with the ferrocene ring was utilized as a chiral ligand for catalytic asymmetric reduction of acetophenone.