Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Addition Compounds of Alkali Metal Hydrides. 32. A Comparison Study of Chiral Trialkylborohydrides and Chiral Dialkylmonoalkoxyborohydrides for the Asymmetric Reduction of Prochiral Ketones: The Effect of Comparable Chiral Alkyl and Alkoxy Groups on Asymmetric Industion$^\dag$

  • Brow, Hervert C. (H.C. Brown and R.B. Wetherill Laboratories of Chemistry, Purdue University) ;
  • Park, Won-Suh (H.C. Brown and R.B. Wetherill Laboratories of Chemistry, Purdue University) ;
  • Cho, Byung-Tae (H.C. Brown and R.B. Wetherill Laboratories of Chemistry, Purdue University)
  • Published : 1987.08.20
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Abstract

Several chiral potassium B-alkyl-9-boratabicyclo[3.3.1]nonanes $(K\; B-R^*-9-BBNH)$ and potassium B-alkoxy-9-boratabicyclo[3.3.1]nonanes $(K \;B-OR^*-9-BBNH)$ were synthesized by treatment of the corresponding trialkylboranes and dialkylmonoalkoxyboranes with a small excess of potassium hydride. The chiral B-alkoxy derivatives generally reduce representative ketones, such as acetophenone and 3-methyl-2-butanone, with greater optical induction than the corresponding B-alkyl derivatives, suggesting the involvement of the oxygen atom in the control process for asymmetric synthesis.

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References

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  1. Homolytic reactions of ligated boranes. Part 16. Enantioselective hydrogen-atom abstraction by chiral amine–boryl radicals: catalytic kinetic resolution of esters and of camphor vol.1993, pp.4, 1987, https://doi.org/10.1039/p29930000665