Chiral synthesis via organoboranes. 14. Selective reductions. 41. Diisopinocampheylchloroborane, an exceptionally efficient chiral reducing agent

…, J Chandrasekharan, PV Ramachandran

Index: Brown, Herbert C.; Chandrasekharan, J.; Ramachandran, P. V. Journal of the American Chemical Society, 1988 , vol. 110, # 5 p. 1539 - 1546

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Citation Number: 314

Abstract

Abstract: Diisopinocampheylchloroborane, readily prepared in both enantiomers in high chemical and optical purities (99% ee) via hydroboration followed by treatment with dry hydrogen chloride in ethyl ether, reduces prochiral ketones at convenient rates in tetrahydrofuran at-25 OC. Reduction of simple dialkyl ketones, 2-butanone, 2-octanone, and 3-methyl-2-butanone, yields the corresponding alcohols with 4%, 7%, and 32% optical ...