title: Enantioselective synthesis of benzoindolizidine derivatives using chiral phase-transfer catalytic intramolecular domino aza-Michael addition/alkylation.
abstract: An efficient and enantioselective strategy to synthesize benzoindolizidines from α,β-unsaturated amino ketones via domino intramolecular aza-Michael addition/alkylation was developed. These reactions were enabled by cinchona alkaloid-derived quaternary ammonium salts as the phase-transfer catalyst. A variety of benzoindolizidines were prepared in good yields (up to 93%) and enantioselectivities (up to 92.8:7.2 er).
authors.affiliation: State Key Laboratory of Analytical Chemistry for Life Science, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China. yushouyun@nju.edu.cn.
authors.forename: Jiajia
authors.initials: J
authors.lastname: Guo
authors.forename: Shouyun
authors.initials: S
authors.lastname: Yu
mesh_terms: D000478:Alkylation; D001372:Aza Compounds / Q000737:chemistry*; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D054836:Indolizidines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D001372:Aza Compounds; D054836:Indolizidines