Chiral Lewis acid-bonded picolinaldehyde enables enantiodivergent carbonyl catalysis in the Mannich/condensation reaction of glycine ester
Xia Zhong, Ziwei Zhong, Zhikun Wu, Zhen Ye, Yuxiang Feng, Shunxi Dong, Xiaohua Liu, Qian Peng, Xiaoming Feng
Abstract
changing the sub-structures of the chiral ligands. The reaction could be carried out in a three-component version involving glycine ester, aldehydes, and anilines with equally good results. Based on control experiments, the X-ray crystal structure study and theoretical calculations, a possible dual-activation mechanism and stereo-control modes were provided to elucidate carbonyl catalysis and enantiodivergence.
Topics & Concepts
AldimineCatalysisChemistryMannich reactionGlycineLewis acids and basesLewis acid catalysisCondensationOrganic chemistryEnantioselective synthesisChiral Lewis acidMedicinal chemistryStereochemistryAmino acidPhysicsThermodynamicsBiochemistryAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry MethodsChemical Synthesis and Reactions