Enantio- and diastereoselective synthesis of homopropargyl amines by copper-catalyzed coupling of imines, 1,3-enynes, and diborons

Manna, Srimanta, Dherbassy, Quentin, Perry, Gregory J.P. and Procter, David J. (2020) Enantio- and diastereoselective synthesis of homopropargyl amines by copper-catalyzed coupling of imines, 1,3-enynes, and diborons. Angewandte Chemie - International Edition, 59 (12), 4879-4882. (doi:10.1002/anie.201915191).

Record type: Article

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.

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Angew Chem Int Ed - 2020 - Manna - Enantio‐ and Diastereoselective Synthesis of Homopropargyl Amines by Copper‐Catalyzed - Version of Record

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e-pub ahead of print date: 9 January 2020

Additional Information: Funding Information: We thank the EPSRC (Established Career Fellowship to D.J.P.; EP/M005062/1), the European Union Horizon 2020 (Fellowship to S.M.; Marie Sklodowska‐Curie grant 798846‐CuCAN), the Leverhulme Trust (PDRA to Q.D.; RPG‐2016‐360), and the University of Manchester (Lectureship to G.J.P.P.).

Keywords: 1,3-enynes, asymmetric catalysis, borylative coupling, copper, homopropargyl amines