The University of Southampton
University of Southampton Institutional Repository

Synergistic catalysis: highly diastereoselective benzoxazole addition to Morita–Baylis-Hillman carbonates

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.
1359-7345
7447-7450
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
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), 7447-7450. (doi:10.1039/c4cc00728j).

Record type: Article

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.

Text
C4CC00728J.pdf - Author's Original
Download (1MB)

More information

e-pub ahead of print date: 20 May 2014
Published date: 20 May 2014
Organisations: Chemistry

Identifiers

Local EPrints ID: 367401
URI: http://eprints.soton.ac.uk/id/eprint/367401
ISSN: 1359-7345
PURE UUID: bffe438a-57f2-49e5-87a5-3edaf0329f4f
ORCID for Marta Meazza: ORCID iD orcid.org/0000-0003-4382-0626
ORCID for Mateusz B. Pitak: ORCID iD orcid.org/0000-0002-3680-7100
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

Catalogue record

Date deposited: 29 Jul 2014 12:08
Last modified: 07 Oct 2020 07:33

Export record

Altmetrics

Contributors

Author: Victor Ceban
Author: Piotr Putaj
Author: Marta Meazza ORCID iD
Author: Mateusz B. Pitak ORCID iD
Author: Simon J. Coles ORCID iD
Author: Jan Vesely
Author: Ramon Rios ORCID iD

University divisions

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of http://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×