Asymmetric synthesis of tetrasubstituted cyclic amines <i>via</i> aza-Henry reaction using cinchona alkaloid sulfonamide/zinc(<scp>ii</scp>) catalysts
Naoki Yasukawa, Ami Yamanoue, Tsunayoshi Takehara, Takeyuki Suzuki, Shuichi Nakamura
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.
Topics & Concepts
CinchonaSulfonamideChemistryCatalysisAlkaloidZincCombinatorial chemistryOrganic chemistryCinchona AlkaloidsEnantioselective synthesisMedicinal chemistryAsymmetric Synthesis and CatalysisSynthesis and Catalytic ReactionsChemical Synthesis and Analysis