Enantioselective synthesis of benzoindolizidine derivatives using chiral phase-transfer catalytic intramolecular domino aza-Michael addition/alkylation. Issue 4 (27th November 2014)

• Record Type: Journal Article
• Authors: Guo, Jiajia; Yu, Shouyun
• Is Part Of: Organic & biomolecular chemistry. Volume 13:Issue 4(2015)
• Page Start: 1179
• Page End: 1186
• Publication Date: 2014-11-27
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c4ob02227k
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : An efficient and enantioselective strategy to synthesize benzoindolizidines via domino intramolecular aza-Michael addition/alkylation was developed. 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).