Enantioselective Construction of Amino Carboxylic‐Phosphonic Acid Derivatives Enabled by Chiral Amino Thiourea‐Catalyzed Decarboxylative Mannich Reaction
Xueqi Wang, Fangfang Feng, Jing Nie, Fa‐Guang Zhang, Jun‐An Ma
Abstract
Abstract An asymmetric decarboxylative Mannich reaction of phosphonate sultam‐ketimines with malonic acid half esters is developed enabled by saccharide‐derived bifunctional amino thiourea catalysis. This protocol provides access to a broad range of α‐amino‐β‐carboxylic phosphonates featuring the N , P ‐containing tetrasubstituted stereocenters with 78–99% ee. Further synthetic derivatizations could allow the introduction of amide, alcohol, and azetidine scaffolds to the core structures. magnified image
Topics & Concepts
ChemistryEnantioselective synthesisThioureaBifunctionalMannich reactionStereocenterOrganocatalysisOrganic chemistryCatalysisAmideAmino acidPhosphonateAlcoholCarboxylic acidCombinatorial chemistryBiochemistryOrganophosphorus compounds synthesisSynthesis and Catalytic ReactionsAsymmetric Synthesis and Catalysis