Synergistic catalysis: highly enantioselective cascade reaction for the synthesis of dihydroacridines
Synergistic catalysis: highly enantioselective cascade reaction for the synthesis of dihydroacridines
We report the first stereoselective synthesis of dihydroacridines through synergistic catalysis, achieving the final target compounds with good to excellent yields and good to excellent enantioselectivities and diastereoselectivities. The synergistic approach consists in an activation of substituted quinolines with a Lewis acid catalyst that react in a cascade fashion with enals activated in the iminium form. Mechanistic calculations support the consecutive Michael‐aldol reaction, followed by dehydration.
7623-7627
Meninno, Sara
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Meazza, Marta
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Yang, Jung Woon
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Tejero, T
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Merino, Pedro
a42d7ef1-fc02-49f4-8837-1294b32b6b9f
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
June 2019
Meninno, Sara
f48711ce-ac34-4c1a-b9ee-6bec2a93c91b
Meazza, Marta
c4665645-8c77-4cfd-aa02-6bcc3341c1aa
Yang, Jung Woon
70327194-b21c-402c-83c0-4474fb47db63
Tejero, T
90bc4a8d-545c-4508-8d7b-9447cfe6d38b
Merino, Pedro
a42d7ef1-fc02-49f4-8837-1294b32b6b9f
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Meninno, Sara, Meazza, Marta, Yang, Jung Woon, Tejero, T, Merino, Pedro and Rios, Ramon
(2019)
Synergistic catalysis: highly enantioselective cascade reaction for the synthesis of dihydroacridines.
Chemistry - A European Journal, 25 (32), .
(doi:10.1002/chem.201901498).
Abstract
We report the first stereoselective synthesis of dihydroacridines through synergistic catalysis, achieving the final target compounds with good to excellent yields and good to excellent enantioselectivities and diastereoselectivities. The synergistic approach consists in an activation of substituted quinolines with a Lewis acid catalyst that react in a cascade fashion with enals activated in the iminium form. Mechanistic calculations support the consecutive Michael‐aldol reaction, followed by dehydration.
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Accepted/In Press date: 1 April 2019
e-pub ahead of print date: 9 April 2019
Published date: June 2019
Identifiers
Local EPrints ID: 431444
URI: http://eprints.soton.ac.uk/id/eprint/431444
ISSN: 0947-6539
PURE UUID: db0e06f2-41cb-4d8c-8269-bb80c6757c45
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Date deposited: 03 Jun 2019 16:30
Last modified: 16 Mar 2024 07:47
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Contributors
Author:
Sara Meninno
Author:
Marta Meazza
Author:
Jung Woon Yang
Author:
T Tejero
Author:
Pedro Merino
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