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Issue 13, 1998
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Synthesis of 3,3′-, 6,6′- and 3,3′,6,6′-substituted binaphthols and their application in the asymmetric hydrophosphonylation of aldehydes—an obvious effect of substituents of BINOL on the enantioselectivity

Abstract

By using a direct ortho-lithiation strategy and/or Ni-catalysed coupling reaction, we have conveniently synthesized three new chiral polysubstituted BINOLs of vast synthetic potential from (S )-BINOL 1 in reasonable yields. Moreover, we have examined closely their influence on the enantioselectivity of the asymmetric Pudovik reaction catalyzed by chiral binaphthol-modified lanthanum alkoxides. The results show that the steric bulk of 3,3′-substituents of BINOL is responsible for a lowering of the enantioselectivity of the reaction, while coordination between the oxygens of the ortho-substituents and the lanthanum ion is beneficial in improving the asymmetric induction. 6,6′-Diphenyl-BINOL has the advantage over simple BINOL in giving the best asymmetric results. Further studies on this aspect are in progress.

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J. Chem. Soc., Perkin Trans. 1, 1998, 2097-2104
Article type
Paper

Synthesis of 3,3′-, 6,6′- and 3,3′,6,6′-substituted binaphthols and their application in the asymmetric hydrophosphonylation of aldehydes—an obvious effect of substituents of BINOL on the enantioselectivity

C. Qian, T. Huang, C. Zhu and J. Sun, J. Chem. Soc., Perkin Trans. 1, 1998, 2097
DOI: 10.1039/A800146D

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