Direct Asymmetric α‐C Addition of Glycinate to Nitroalkenes by Pyridoxal/Nd Dual Catalysis
Abstract
Abstract Direct enantioselective α‐C Michael addition of NH 2 ‐unprotected glycinate to nitroalkenes is a significant organic transformation, which may provide a highly efficient strategy to make bioactive chiral γ‐nitro‐α‐amino acid esters. However, it is extremely challenging to achieve this reaction due to the interference of the reactive NH 2 group, potential [3 + 2] cycloaddition side reaction and complicated stereoselective control. Carbonyl catalysis is an effective strategy to activate glycinate by forming an imine to facilitate the conjugate addition. With a pyridoxal/Nd dual catalytic system, direct asymmetric α‐C conjugate addition of glycinate to nitroalkenes has been successfully developed for the first time, producing a broad range of chiral γ‐nitro‐α‐amino acid esters in high yields with excellent stereoselectivities (up to 98% yield, >20:1 dr, 98% ee). The products can be easily converted into various biologically significant chiral molecules maintaining the same enantiopurity.
Article Details
Authors (7)
Shibo Si
The Education Ministry Key Lab of Resource Chemistry, Shanghai Frontiers Science Center of Biomimetic Catalysis, and College of Chemistry and Materials Science Shanghai Normal University Shanghai 200234 China
Qingfang Wang
The Education Ministry Key Lab of Resource Chemistry, Shanghai Frontiers Science Center of Biomimetic Catalysis, and College of Chemistry and Materials Science Shanghai Normal University Shanghai 200234 China
Yiming Lv
The Education Ministry Key Lab of Resource Chemistry, Shanghai Frontiers Science Center of Biomimetic Catalysis, and College of Chemistry and Materials Science Shanghai Normal University Shanghai 200234 China
Huifang Liao
The Education Ministry Key Lab of Resource Chemistry, Shanghai Frontiers Science Center of Biomimetic Catalysis, and College of Chemistry and Materials Science Shanghai Normal University Shanghai 200234 China
Wen‐Wen Chen
The Education Ministry Key Lab of Resource Chemistry, Shanghai Frontiers Science Center of Biomimetic Catalysis, and College of Chemistry and Materials Science Shanghai Normal University Shanghai 200234 China
Siqi Liu
Baoguo Zhao
The Education Ministry Key Lab of Resource Chemistry, Shanghai Frontiers Science Center of Biomimetic Catalysis