Asymmetric α-alkylation of cyclic β-keto esters and β-keto amides by phase-transfer catalysis

Without employing any transition metal, a highly enantioselective α-alkylation of cyclic β-keto esters and β-keto amides has been realized by phase-transfer catalysis. This improved procedure is applicable to different kinds of halides with cinchona derivatives and gives the corresponding products i...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2019-01, Vol.17 (3), p.573-584
Main Authors: Wang, Yakun, Li, Yueyun, Lian, Mingming, Zhang, Jixia, Liu, Zhaomin, Tang, Xiaofei, Yin, Hang, Meng, Qingwei
Format: Article
Language:English
Subjects:
Alkylation
Alliances
Amides
Carbonyl compounds
Catalysis
Chemical industry
Enantiomers
Esters
Halides
Phase transfer catalysts
Transition metals
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Summary:Without employing any transition metal, a highly enantioselective α-alkylation of cyclic β-keto esters and β-keto amides has been realized by phase-transfer catalysis. This improved procedure is applicable to different kinds of halides with cinchona derivatives and gives the corresponding products in excellent enantiopurities (up to 98% ee) and good yields (up to 98%). Moreover, the reaction was scalable and the phase-transfer catalyst was recyclable. This provided an alternative and competitive method to the asymmetric α-alkylation of β-dicarbonyl compounds.
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob02669f