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Paper | Regular issue | Vol 27, No. 7, 1988, pp.1713-1717
Published online, 1st January, 1970
DOI: 10.3987/COM-88-4575
Enantioselective Reduction of Racemic Epoxides with the Chiral 9-Alkoxy-9-borabicyclo[3.3.1]nonane-Potassium Hydride and Chiral Potassium 9-Alkoxy-9-boratabicyclo[3.3.1]nonane Systems

Jin Soon Cha,* Kwang Woo Lee, Mal Sook Yoon, and Jae Cheol Lee

*Department of Chemistry, Yeungnam University, Kyongsan 712-749, Korea


The chiral 9-alkoxy-9-borabicyclo[3.3.1]nonane (1 and 2)-potassium hydride and chiral potassium 9-alkoxy-9-boratabicyclo[3.3.1]nonane (3 and 4) systems were applied to the enantioselective reduction (resolution) of representative racemic epoxides, such as 1,2-epoxybutane, 1,2-epoxyoctane, 3,3-dimethyl-1,2-epoxybutane, and styrene oxide. The enantioselectivity by 1-KH and 2-KH systems was in the range of 9.8-46.3% ee. The corresponding chiral borhydrides, 3 and 4, resolved racemic epoxides examined in the range of 9.8-43.3% ee. All the reduction products were consistently enriched in the enantiomer with levoratation.