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Acetylphosphonate as a surrogate of acetate or acetamide in organocatalyzed enantioselective aldol reactions.

ABSTRACT: Highly enantioselective aldol reactions of acetylphosphonates and activated carbonyl compounds was realized with cinchona alkaloid derived catalysts, in which the acetylphosphonate was directly used as an enolate precursor for the first time. The aldol product obtained was converted in situ to its corresponding ester or amide through methanolysis or aminolysis. The overall process may be viewed as formal highly enantioselective acetate or acetamide aldol reactions, which are very difficult to achieve directly with organocatalytic methods.

SUBMITTER: Guang J

PROVIDER: S-EPMC3426636 | biostudies-literature | 2012 Jun

REPOSITORIES: biostudies-literature

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Acetylphosphonate as a surrogate of acetate or acetamide in organocatalyzed enantioselective aldol reactions.

Guang Jie J Guo Qunsheng Q Zhao John Cong-Gui JC

Organic letters 20120531 12

Highly enantioselective aldol reactions of acetylphosphonates and activated carbonyl compounds was realized with cinchona alkaloid derived catalysts, in which the acetylphosphonate was directly used as an enolate precursor for the first time. The aldol product obtained was converted in situ to its corresponding ester or amide through methanolysis or aminolysis. The overall process may be viewed as formal highly enantioselective acetate or acetamide aldol reactions, which are very difficult to ac ...[more]

PMID: 22650245

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