Diastereoselectivity of Enolate Anion Protonation. H/D Exchange of β-Substituted Ethyl Butanoates in Ethanol-d

…, JW Apostol, M Bastienaansen, JW Evans…

文献索引：Mohrig, Jerry R.; Rosenberg, Robert E.; Apostol, John W.; Bastienaansen, Mark; Evans, Jordan W.; Franklin, Sonya J.; Frisbie, C. Daniel; Fu, Sabrina S.; Hamm, Michelle L.; Hirose, Christopher B.; Hunstad, David A.; James, Thomas L.; King, Randall W.; Larson, Christopher J.; Latham, Hallie A.; Owen, David A.; Stein, Karin A.; Warnet, Ronald Journal of the American Chemical Society, 1997 , vol. 119, # 3 p. 479 - 486

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被引用次数: 38

摘要

The stereochemistry of base-catalyzed H/D exchange on 13 β-substituted ethyl butanoates in ethanol-d has been studied in order to analyze the steric and electronic factors which control the diastereoselectivity of electrophilic attack on enolate anions. Electrophilic deuteration of the enolate anion also determines the stereoselectivity of 1, 4-conjugate addition of ethanol-d to α, β-unsaturated esters. Experimental conditions were selected ...