Catalytic, Enantioselective Bifunctional Inverse Electron Demand Hetero-Diels−Alder Reactions of Ketene Enolates and o-Benzoquinone Diimides

• Published in: Journal of the American Chemical Society Vol. 128; no. 41; pp. 13370 - 13371
• Main Authors: Abraham, Ciby J, Paull, Daniel H, Scerba, Michael T, Grebinski, James W, Lectka, Thomas
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 18-10-2006
• Subjects: Alcohols - chemistry; Alkadienes - chemistry; Benzoquinones - chemistry; Catalysis; Chemistry; Electrons; Ethylenes - chemistry; Exact sciences and technology; General and physical chemistry; Imides - chemistry; Ketones - chemistry; Models, Chemical; Noncondensed benzenic compounds; Organic chemistry; Preparations and properties; Stereoisomerism; Imide; Catalytic reaction; Enantioselectivity; Benzoquinone derivatives; Bifunctional compound; Benzenic compound; Enolate; Ketenes; Diimide
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja065754d

In this Communication, we report a system in which an achiral Lewis acid (activating the diene) works in concert with a chiral nucleophile (dienophile) to effect the first highly enantio- and regioselective catalytic inverse electron demand Diels−Alder [4 + 2] cycloaddition reaction to form biologically active quinoxalinones from ketene enolates and o-benzoquinone diimides in good to excellent yields with >99% ee.