• Title/Summary/Keyword: Trialkylboranes

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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.;Park, Won-Suh;Cho, Byung-Tae
    • Bulletin of the Korean Chemical Society
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    • v.8 no.4
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    • pp.276-280
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    • 1987

  • 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.

  • https://doi.org/10.5012/bkcs.1987.8.4.276 인용 PDF