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Asymmetric Reduction of Prochiral Ketones with Potassium 9-O-isopinocampheyloxy-9 boratabicyclo[3.3.1]nonane$^+$
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  • Asymmetric Reduction of Prochiral Ketones with Potassium 9-O-isopinocampheyloxy-9 boratabicyclo[3.3.1]nonane$^+$
저자명
Park. Won-Suh,Cho. Byung-Tae,Cha. Jin-Soon
간행물명
Bulletin of the Korean Chemical Society
권/호정보
1987년|8권 3호|pp.211-214 (4 pages)
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이 논문은 한국과학기술정보연구원과 논문 연계를 통해 무료로 제공되는 원문입니다.
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기타언어초록

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 -$78^{circ}C$. 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.