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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 8, Number 4
April 20, 1987 

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 Asy
Herbert C. Brown*, Won Suh Park, Byung Tae Cho
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.
276 - 280
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