Diastereoselectivity in the reduction of sterically unbiased 2, 2-diarylcyclopentanones

RL Halterman, MA McEvoy

文献索引：Halterman, Ronald L.; McEvoy, Marjorie A. Journal of the American Chemical Society, 1990 , vol. 112, # 18 p. 6690 - 6695

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被引用次数: 59

摘要

Abstract: Reduction of sterically unbiased 2-phenyl-2-(4-X-phenyl) cyclopentanones 1 (X= NOz, Br, CI, OCH3, OH, NH,) with either sodium borohydride in methanol or lithium borohydride in tetrahydrofuran at 0 OC produced diastereomeric cyclopentanols 2 in cis/trans ratios varying from 79: 21 to 30: 70 as determined by IH and I3C NMR spectroscopy. These ratios correspond to an overall energy difference of 1.3 kcal/mol. In ...