Enantioselective copper-catalyzed borylative cyclization for the synthesis of Quinazolinones
Enantioselective copper-catalyzed borylative cyclization for the synthesis of Quinazolinones
Quinazolinones are common substructures in molecules of medicinal importance. We report an enantioselective copper-catalyzed borylative cyclization for the assembly of privileged pyrroloquinazolinone motifs. The reaction proceeds with high enantio- and diastereocontrol, and can deliver products containing quaternary stereocenters. The utility of the products is demonstrated through further manipulations.
asymmetric, boron, copper, cyclization, nitrogen-containing heterocycles
14355-14359
Dherbassy, Quentin
84c92592-f8db-4811-a5ad-f717d554713e
Manna, Srimanta
79e58031-758a-42ae-9110-5ceec8a2f9e9
Shi, Chunling
bbedbddc-883f-4d1a-a678-67a0fd6fa33d
Prasitwatcharakorn, Watcharapon
b7d44200-a55d-46af-8419-2d5f81455926
Crisenza, Giacomo E.M.
3543868c-2fb0-485d-b236-d76bff609e88
Perry, Gregory J.P.
766e7fc8-abf3-4d1e-9949-c1b3439a2185
Procter, David J.
7642b405-d26f-4064-b0d2-8a1d562348b4
21 June 2021
Dherbassy, Quentin
84c92592-f8db-4811-a5ad-f717d554713e
Manna, Srimanta
79e58031-758a-42ae-9110-5ceec8a2f9e9
Shi, Chunling
bbedbddc-883f-4d1a-a678-67a0fd6fa33d
Prasitwatcharakorn, Watcharapon
b7d44200-a55d-46af-8419-2d5f81455926
Crisenza, Giacomo E.M.
3543868c-2fb0-485d-b236-d76bff609e88
Perry, Gregory J.P.
766e7fc8-abf3-4d1e-9949-c1b3439a2185
Procter, David J.
7642b405-d26f-4064-b0d2-8a1d562348b4
Dherbassy, Quentin, Manna, Srimanta, Shi, Chunling, Prasitwatcharakorn, Watcharapon, Crisenza, Giacomo E.M., Perry, Gregory J.P. and Procter, David J.
(2021)
Enantioselective copper-catalyzed borylative cyclization for the synthesis of Quinazolinones.
Angewandte Chemie - International Edition, 60 (26), .
(doi:10.1002/anie.202103259).
Abstract
Quinazolinones are common substructures in molecules of medicinal importance. We report an enantioselective copper-catalyzed borylative cyclization for the assembly of privileged pyrroloquinazolinone motifs. The reaction proceeds with high enantio- and diastereocontrol, and can deliver products containing quaternary stereocenters. The utility of the products is demonstrated through further manipulations.
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More information
Accepted/In Press date: 13 April 2021
Published date: 21 June 2021
Additional Information:
Funding Information:
We thank the Leverhulme Trust (PDRA to Q.D.; RPG‐2016‐360), the European Union Horizon 2020 (Fellowship to S.M.; Marie Sklodowska‐Curie grant 798846‐CuCAN), Jiangsu Oversea Visiting Scholar Program for University Prominent Young & Middle‐aged Teachers and Presidents (Funding to C.S.), the Royal Government of Thailand (DPST scholarship to W.P.), and the University of Manchester (Lectureship to G.J.P.P. and G.E.M.C.).
Publisher Copyright:
© 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH
Keywords:
asymmetric, boron, copper, cyclization, nitrogen-containing heterocycles
Identifiers
Local EPrints ID: 477104
URI: http://eprints.soton.ac.uk/id/eprint/477104
ISSN: 1433-7851
PURE UUID: 2c150633-51ab-4377-8164-d98db371342c
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Date deposited: 26 May 2023 16:37
Last modified: 18 Mar 2024 04:11
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Contributors
Author:
Quentin Dherbassy
Author:
Srimanta Manna
Author:
Chunling Shi
Author:
Watcharapon Prasitwatcharakorn
Author:
Giacomo E.M. Crisenza
Author:
Gregory J.P. Perry
Author:
David J. Procter
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