Enantioselective Amine-Catalyzed [4 + 2] Annulations of Allene Ketones and 2,3-Dioxopyrrolidine Derivatives: Synthesis of 4<i>H</i>-Pyran Derivatives

2015/06/23 by Shuang Zhang, Yong-Chun Luo, Yong‐Chun Luo +8 · 1 citation
Chemistry · #Synthetic Organic Chemistry Methods #Catalytic Alkyne Reactions #Asymmetric Synthesis and Catalysis

paper · doi:10.1021/acs.joc.5b00961

Abstract

An efficient cinchona alkaloid-derived amine catalyzed asymmetric [4 + 2] cycloaddition is successfully developed. 4H-Pyran fused pyrrolin-2-one products are readily obtained in moderate to high yields with good enantioselectivites by employing allene ketones and 2,3-dioxopyrrolidine derivatives as substrates.

Cited by

• Enantioselective Hetero-Diels–Alder Reaction and the Synthesis of Spiropyrrolidone Derivatives

Related

• Chiral Isochalcogenourea‐Catalysed Enantioselective (4+2) Cycloadditions of Allenoates
• Recent Advances in the Enantioselective Synthesis of Chiral Amines via Transition Metal-Catalyzed Asymmetric Hydrogenation
• Organocatalytic Enantioselective Synthesis of Chiral Spiro‐indoline‐pyrazolones through a formal [4+1] Annulation Reaction of 4‐Bromopyrazolones and aza‐<i>ortho</i>‐Quinone Methides
• An Asymmetric Variant of the Bischler–Möhlau Indole Synthesis*
• Regioselectivity Switch between Enantioselective 1,2- and 1,4-Addition of Allyl Aryl Ketones with 2,3-Dioxopyrrolidines