Double Molecular Recognition with Aminoorganoboron Complexes: Selective Alcoholysis of β-Dicarbonyl Derivatives


  • This work was supported by a Grant-in-Aid for Scientific Research B (General) from the JSPS, Scientific Research on Priority Areas “Advanced Molecular Transformations of Carbon Resource” from the MEXT, and the GCOE. S.O. thanks the JSPS fellowship for young scientists. The authors wish to thank Prof. R. Noyori (Nagoya University & RIKEN) for helpful discussions.


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Double duty: Aminoorganoboron (AOB) complexes recognize alcohol and β-dicarbonyl units, and thereby facilitate chemo- and site-selective alcoholysis of the latter (see scheme). The complex activates both reaction partners. This strategy enables C[BOND]C, C[BOND]N, and C[BOND]O bond cleavage in addition/elimination reactions under near neutral pH conditions and provides a new method for functional group conversions.