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Paper | Regular issue | Vol 27, No. 6, 1988, pp.1455-1460
Published online, 1st January, 1970
DOI: 10.3987/COM-88-4549
Preparation of Potassium 9-Alkyl-9-bortabicyclo[3.3.1]nonanes and Their Stereoselectivity in the Reduction of Cyclic Ketones

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

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


Potassium 9-alkyl-9-boratabicyclo[3.3.1]nonanes (K 9-R-9-BBNHs) possessing a wide range of steric requirements were prepared from the reaction of the corresponding 9-alkyl-9-borabicyclo[3.3.1]nonanes (9-R-9-BBNs) and excess potassium hydride, and the stereoselectivities of these reagents in the reduction of representative cyclic ketones were examined. All reagents showed high stereoselectivities, with the stereoselectivities generally increasing with increasing steric requirements of the alkyl substituent. Especially, the tert-butyl derivative, K 9-TB-BBNH, achieved the most favorable stereoselectivity, comparable to that by lithium trisiamylborohydride at 0°C.