期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 135, 期 17, 页码 6677-6693出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja402058v
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资金
- Deutsche Forschungsgemeinsschaft (DFG)
- Max-Planck-Gesellschaft (MPG)
- Fonds der Chemischen Industrie (FCI)
Using cinchona alkaloid-derived primary amines as catalysts and aqueous hydrogen peroxide as, the oxidant, we have developed highly enantioselective Weitz-Scheffer-type epoxidation and hydroperoxidation reactions of alpha,beta-unsaturated carbonyl compounds (up to 99.5:0.5 er). In this article, we present our full studies on this family of reactions, employing acyclic enones, 5-15-membered cyclic enones, and alpha-branched enals as substrates. In addition to an expanded scope, synthetic applications of the products are presented. We also report detailed mechanistic investigations of the catalytic intermediates, structure-activity relationships of the cinchona amine catalyst, and rationalization of the absolute stereoselectivity by NMR spectroscopic studies and DFT calculations.
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