Cinchona Alkaloid Catalyzed Regio‐ and Enantioselective Allylic Amination of Morita–Baylis–Hillman Carbonates with Isatins

Abstract

AbstractAn efficient enantioselective allylic amination of Morita–Baylis–Hillman (MBH) carbonates derived from methyl acrylate and aromatic aldehydes with isatins has been realized in the presence of commercially available cinchona alkaloids. The allylic amination products were obtained in moderate‐to‐good yields (46–74 %) with moderate‐to‐good enantioselectivities (up to 89 % ee) under mild conditions. The synthetic utility of the amination products has been well demonstrated by the facile synthesis of methyl (3R,4R)‐10‐oxo‐4‐phenyl‐2,3,4,10‐tetrahydropyrimido[1,2‐a]indole‐3‐carboxylate.