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Korean Chemical Society (대한화학회)
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Selective Reduction of Carbonyl Compounds with B-Acetoxy- and B-Trifluoroacetoxydiisopinocampheylboranes

  • Cha, Jin-Soon (Department of Chemistry and Institute of Natural Sciences, Yeungnam University) ;
  • Nam, Ho-Tae (Department of Chemistry and Institute of Natural Sciences, Yeungnam University) ;
  • Park, Seung-Jin (Department of Chemistry and Institute of Natural Sciences, Yeungnam University) ;
  • Kwon, Sang-Yong (Department of Chemistry and Institute of Natural Sciences, Yeungnam University) ;
  • Kwon, Oh Oun (Department of Chemistry and Institute of Natural Sciences, Yeungnam University)
  • Published : 2006.05.20
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Abstract

The new MPV-type reagents, B-acetoxydiisopinocampheylborane ($Ipc _2$BOAc) and B-trifluoroacetoxydiisopinocampheylborane $(Ipc _2BO _2CCF _3)$, have been prepared and their reducing characteristics in the reduction of carbonyl compound have been examined in order to find out a new reducing system with unique applicability in organic synthesis. In general, the reactivity of $Ipc _2BO _2CCF _3$ appears to be stronger than that of $Ipc _2$BOAc, presumably due to the acidity increase by the electron-withdrawing fluorine-substituent. Both reagents show an excellent selectivity in 1,2-reduction of $\alpha,\beta$-unsaturatedcarbonyl compounds and in competitive reduction between structurally different carbonyl compounds. In addition, $Ipc _2BO _2CCF _3$ shows interesting features in the stereoreduction of cyclic ketones.

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References

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