Chiral Primary Amine Catalyzed Enantioselective Tandem Reactions Based on Heyns Rearrangement: Synthesis of α-Tertiary Amino Ketones
Xiao‐kang Nie, Yue Chen, Shiqi Zhang, Xin Cui, Zhuo Tang, Guangxun Li
Abstract
Herein, we disclose a new catalytic asymmetric tandem reaction based on the Heyns rearrangement for the synthesis of chiral α-amino ketones with readily available substrates. The rearrangement is different from the Heyns rearrangement in that the α-amino ketones were obtained without the shift of the carbonyl group. The key to success is using chiral primary amine as a catalyst by mimicking glucosamine-6-phosphate synthase in catalyzing the efficient Heyns rearrangement in organisms.
Topics & Concepts
ChemistryEnantioselective synthesisAmine gas treatingCatalysisTandemStereochemistryPrimary (astronomy)Organic chemistryCombinatorial chemistryAstronomyComposite materialMaterials sciencePhysicsSynthesis and Catalytic ReactionsAsymmetric Synthesis and CatalysisAsymmetric Hydrogenation and Catalysis