Enantioselective A3 -Coupling Reaction Employing Chiral CuI - i PrpyboxdiPh/ N-Boc-(l)-Proline Complex under Cooperative Catalysis: Application in the Synthesis of (Indol-2-yl)methanamines

The Journal of Organic Chemistry
Sivasankaran DhanasekaranVinod K Singh

Abstract

An efficient route to enantioenriched propargylamines via a three-component alkynylation reaction using cooperative catalysis with a CuI- iPrpyboxdiPh complex and N-Boc-(l)-proline has been accomplished. A variety of functionalized amines, aldehydes, and 2-ethynyl anilines were reacted smoothly at ambient temperature to furnish a wide range of propargylamines in high yields (up to 94%) and excellent enantioselectivities (up to 98% ee). Synthetic utility of the methodology has been demonstrated by transforming the products into various synthetically useful intermediates. Finally, propargylamines were transformed into biologically important (indol-2-yl)methanamines over two steps in good yields (up to 88%) with an excellent level of enantioselectivities (up to 95%).

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Citations

Aug 30, 2019·Chemical Society Reviews·Balaji V RokadePatrick J Guiry
Sep 26, 2019·Chemistry : a European Journal·Alessandro CerveriMarco Bandini
Nov 23, 2021·The Journal of Organic Chemistry·Fabian SchlimpenStefan Chassaing

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