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

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

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.

1,3-enynes, asymmetric catalysis, borylative coupling, copper, homopropargyl amines
1433-7851
4879-4882
Manna, Srimanta
79e58031-758a-42ae-9110-5ceec8a2f9e9
Dherbassy, Quentin
84c92592-f8db-4811-a5ad-f717d554713e
Perry, Gregory J.P.
766e7fc8-abf3-4d1e-9949-c1b3439a2185
Procter, David J.
7642b405-d26f-4064-b0d2-8a1d562348b4
Manna, Srimanta
79e58031-758a-42ae-9110-5ceec8a2f9e9
Dherbassy, Quentin
84c92592-f8db-4811-a5ad-f717d554713e
Perry, Gregory J.P.
766e7fc8-abf3-4d1e-9949-c1b3439a2185
Procter, David J.
7642b405-d26f-4064-b0d2-8a1d562348b4

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.

Text
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

Identifiers

Local EPrints ID: 478072
URI: http://eprints.soton.ac.uk/id/eprint/478072
ISSN: 1433-7851
PURE UUID: fe7b0cdc-ceee-4330-b963-e0d9b1db4cb9
ORCID for Gregory J.P. Perry: ORCID iD orcid.org/0000-0001-8173-3369

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Date deposited: 21 Jun 2023 16:53
Last modified: 06 Jun 2024 02:17

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Contributors

Author: Srimanta Manna
Author: Quentin Dherbassy
Author: Gregory J.P. Perry ORCID iD
Author: David J. Procter

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