Asymmetric α-alkylation of cyclic β-keto esters and β-keto amides by phase-transfer catalysis. Issue 3 (21st December 2018)

• Record Type: Journal Article
• Authors: Wang, Yakun; Li, Yueyun; Lian, Mingming; Zhang, Jixia; Liu, Zhaomin; Tang, Xiaofei; Yin, Hang; Meng, Qingwei
• Is Part Of: Organic & biomolecular chemistry. Volume 17:Issue 3(2018)
• Page Start: 573
• Page End: 584
• Publication Date: 2018-12-21
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob02669f
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A facile and efficient asymmetric α-alkylation of β-keto esters and β-keto amides has been achieved by phase-transfer catalysis. Abstract : 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.