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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 8, Number 3
March 20, 1987 

Asymmetric Reduction of Prochiral Ketones with Potassium 9-O-isopinocampheyloxy-9-boratabicyclo[3.3.1]nonane
Won Suh Park, Byung Tae Cho, Jin Soon Cha
Asymmetric reduction of a series of aliphatic ketones and representative other classes of ketones with potassium 9-O-isopinocampheyloxy-9-boratabicyclo[3.3.1]non ane (K 9-O-Ipc-9-BBNH) was studied. All the ketones examined were reduced smoothly to the corresponding alcohols in THF at -78℃. Thus, the reduction of 2-butanone, 3-methyl-2-butanone, 3,3-dimethyl-2-butanone, 2-octanone, and 4-phenyl-2-butanone provides 51% ee, 61% ee, 44% ee, 35% ee, and 33% ee of optical inductions, respectively. The reduction of other classes of ketones gave 52% ee for 2,2-dimethylcyclopentanone, 47% ee for acetophenone, 23% ee for 3-acetylpyridine, 50% ee for methyl benzoylformate, 4.8% ee for 2-chloroacetophenone, 30% ee for trans-4-phenyl-3-butene-2-one, and 2% ee for 4-phenyl-3-butyn-2-one. Thus, the reagent was found to be most useful in the asymmetric reduction of acyclic and cyclic aliphatic series of ketones.
211 - 214
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