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Chiral β-diols, diamines and amino alcohols are significantly important compounds in asymmetric reaction. These compounds were prepared by samarium diiodide-mediated reductive coupling of planar chiral transition metal complexes. Planar chiral ortho-substituted benzaldehyde tricarbonyl chromium complexes were treated with samarium diiodide to give optically pure β-diols. Similarly, planar chiral benzaldimine chromium complexes afforded β-diamines in enantiopure form. Furthermore, reductive cross-coupling of planar chiral aldehydes with N-tosyl aldimines gave optically pure β-amino alcohols without formation of homo-coupling products. Thus, samarium diiodide-mediated reductive cross-coupling of N-tosylferrocenylideneamines with planar chiral ferocenecarboxaldehydes or benzaldehyde chromium complexes gave optically pure anti-β-amino alcohols. On the other hand, the reductive cross coupling of N-tosyl benzylideneamines with planar chiral aldehydes afforded optically pure syn-β-amino alcohols.

Synthesis of Optically Active .BETA.-Diols, Diamines and Amino Alcohols by Reductive Coupling of Planar Chiral Transition Metal Complexes