Synergistic catalysis: highly diastereoselective benzoxazole addition to Morita–Baylis-Hillman carbonates
Synergistic catalysis: highly diastereoselective benzoxazole addition to Morita–Baylis-Hillman carbonates
An expedited method has been developed for the diastereoselective synthesis of highly functionalized alkyl-azaarene systems with good yields and high diastereoselectivities (>15 : 1 dr). The methodology includes a synergistic catalysis event involving organometallic (10 mol% AgOAc) activation of an alkyl azaarene and Lewis base (10 mol% DABCO) activation of a Morita–Baylis–Hillman carbonate. The structure and relative configuration of a representative product were confirmed by X-ray analysis.
7447-7450
Ceban, Victor
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Putaj, Piotr
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Meazza, Marta
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Pitak, Mateusz B.
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Coles, Simon J.
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Vesely, Jan
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Rios, Ramon
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20 May 2014
Ceban, Victor
2e53f2b7-42ff-4c26-96e9-ef75891af166
Putaj, Piotr
52fe3674-7107-4eae-8075-fcd057a93f26
Meazza, Marta
c4665645-8c77-4cfd-aa02-6bcc3341c1aa
Pitak, Mateusz B.
eeb6a00f-2291-4376-830f-d30dfd607ed1
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Vesely, Jan
1853ff19-a906-4321-bd69-f7e434176fc3
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Ceban, Victor, Putaj, Piotr, Meazza, Marta, Pitak, Mateusz B., Coles, Simon J., Vesely, Jan and Rios, Ramon
(2014)
Synergistic catalysis: highly diastereoselective benzoxazole addition to Morita–Baylis-Hillman carbonates.
Chemical Communications, 50 (56), .
(doi:10.1039/c4cc00728j).
Abstract
An expedited method has been developed for the diastereoselective synthesis of highly functionalized alkyl-azaarene systems with good yields and high diastereoselectivities (>15 : 1 dr). The methodology includes a synergistic catalysis event involving organometallic (10 mol% AgOAc) activation of an alkyl azaarene and Lewis base (10 mol% DABCO) activation of a Morita–Baylis–Hillman carbonate. The structure and relative configuration of a representative product were confirmed by X-ray analysis.
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C4CC00728J.pdf
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e-pub ahead of print date: 20 May 2014
Published date: 20 May 2014
Organisations:
Chemistry
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Local EPrints ID: 367401
URI: http://eprints.soton.ac.uk/id/eprint/367401
ISSN: 1359-7345
PURE UUID: bffe438a-57f2-49e5-87a5-3edaf0329f4f
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Date deposited: 29 Jul 2014 12:08
Last modified: 15 Mar 2024 03:01
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Author:
Victor Ceban
Author:
Piotr Putaj
Author:
Marta Meazza
Author:
Mateusz B. Pitak
Author:
Jan Vesely
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