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Enantio‐ and Diastereoselective Synthesis of Homopropargyl Amines by Copper‐Catalyzed Coupling of Imines, 1,3‐Enynes, and Diborons

Srimanta Manna, Quentin Dherbassy, Gregory J. P. Perry, David J. Procter

2020Angewandte Chemie International Edition62 citationsDOIOpen Access PDF

Abstract

An efficient, enantio- and diastereoselective, copper-catalyzed coupling of imines, 1,3-enynes, and diborons is reported. The process shows broad substrate scope and delivers complex, chiral homopropargyl amines; useful building blocks on the way to biologically-relevant compounds. In particular, functionalized homopropargyl amines bearing up to three contiguous stereocenters can be prepared in a single step.

Topics & Concepts

StereocenterChemistryCatalysisCombinatorial chemistryCopperSubstrate (aquarium)Coupling (piping)Scope (computer science)Enantioselective synthesisOrganic chemistryMaterials scienceComputer scienceProgramming languageGeologyMetallurgyOceanographyOrganoboron and organosilicon chemistrySynthetic Organic Chemistry MethodsCatalytic Cross-Coupling Reactions
Enantio‐ and Diastereoselective Synthesis of Homopropargyl Amines by Copper‐Catalyzed Coupling of Imines, 1,3‐Enynes, and Diborons | Litcius