Asymmetric synthesis of tetrasubstituted cyclic amines via aza-Henry reaction using cinchona alkaloid sulfonamide/zinc(ii) catalysts. Issue 9 (24th December 2021)

• Record Type: Journal Article
• Authors: Yasukawa, Naoki; Yamanoue, Ami; Takehara, Tsunayoshi; Suzuki, Takeyuki; Nakamura, Shuichi
• Is Part Of: Chemical communications. Volume 58:Issue 9(2022)
• Page Start: 1318
• Page End: 1321
• Publication Date: 2021-12-24
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d1cc06492d
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Asymmetric aza-Henry reaction of cyclic ketimines, which are easily prepared by the oxidation of commercially available cyclic amino acids with nitroalkanes was accomplished by using our original cinchona alkaloid sulfonamide/zinc(ii ) catalyst. Abstract : The first enantioselective aza-Henry reaction of non-activated cyclic iminoesters, derived from cyclic amino acids, has been developed. Good yields and enantioselectivities were observed for the reaction using our original cinchona alkaloid sulfonamide/zinc(ii ) catalyst. The transition state was proposed to explain the stereoselectivity based on experiments and DFT calculations.