Mechanistic imperatives for catalysis of aldol addition reactions: Partitioning of the enolate intermediate between reaction with Brønsted acids and the carbonyl group

JP Richard, RW Nagorski

文献索引：Richard, John P.; Nagorski Journal of the American Chemical Society, 1999 , vol. 121, # 20 p. 4763 - 4770

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被引用次数: 30

摘要

The lyoxide ion catalyzed intramolecular aldol addition reaction of 2-(2-oxopropyl) benzaldehyde (1) to give the aldol adduct 3 proceeds via essentially irreversible formation of the acetone-like enolate intermediate 2, because reprotonation of 2 by a solvent of H2O or D2O (k HOH or k DOD) is much slower than intramolecular addition of the enolate to the carbonyl group (kc). The aldol addition reaction of 1 catalyzed by high concentrations of 3- ...