The Journal of Organic Chemistry

… synthesis via organoboranes. 15. Selective reductions. 42. Asymmetric reduction of representative prochiral ketones with potassium 9-O-(1, 2: 5, 6-di-O-isopropylidene …

HC Brown, BT Cho, WS Park

Index: Brown, Herbert C.; Cho, Byung Tae; Park, Won Suh Journal of Organic Chemistry, 1988 , vol. 53, # 6 p. 1231 - 1238

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Citation Number: 76

Abstract

Potassium 9-0-(1, 2: 5, 6-di-0-isopropylidene-a-~-glucofura1iosyl)-9-boratabicyclo [3.3. l] nonane (9-0-DIPGF-g-BBNH, K-glucoride), a new stable chiral borohydride reducing agent, was prepared by reaction of the corresponding borinic ester, 9-0-DIPGF-9-BBN, with potassium hydride in THF. The reagent provides high optical induction for asymmetric reduction of prochiral ketones, such as relatively hindered aliphatic ketones, alkyl ...