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Substrate-dependent nonlinear effects in proline-thiourea-catalyzed aldol reactions: unraveling the role of the thiourea co-catalyst

Substrate-dependent nonlinear effects in proline-thiourea-catalyzed aldol reactions: unraveling the role of the thiourea co-catalyst
Substrate-dependent nonlinear effects in proline-thiourea-catalyzed aldol reactions: unraveling the role of the thiourea co-catalyst
The study of nonlinear effects in the proline–thiourea-catalyzed aldol reaction between acetone and aromatic aldehydes, together with NMR and ESI-MS experiments, shows that the main role of the thiourea co-catalyst is that of promoting both the formation of a soluble Seebach's oxazolidinone intermediate and its conversion into the iminium carboxylate isomer.
aldol reaction, nonlinear effects, organocatalysis, proline, thiourea
0947-6539
1142-1148
El-Hamdouni, Niama
f709e58d-ce17-471f-9812-955f5cf0235d
Companyó, Xavier
446791db-6e0a-40f9-9f20-3a8e8af9803c
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa
El-Hamdouni, Niama
f709e58d-ce17-471f-9812-955f5cf0235d
Companyó, Xavier
446791db-6e0a-40f9-9f20-3a8e8af9803c
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Moyano, Albert
07f92405-40f4-4fc4-97b3-9bd5c9c14baa

El-Hamdouni, Niama, Companyó, Xavier, Rios, Ramon and Moyano, Albert (2010) Substrate-dependent nonlinear effects in proline-thiourea-catalyzed aldol reactions: unraveling the role of the thiourea co-catalyst. Chemistry - A European Journal, 16 (4), 1142-1148. (doi:10.1002/chem.200902678). (PMID:20029925)

Record type: Article

Abstract

The study of nonlinear effects in the proline–thiourea-catalyzed aldol reaction between acetone and aromatic aldehydes, together with NMR and ESI-MS experiments, shows that the main role of the thiourea co-catalyst is that of promoting both the formation of a soluble Seebach's oxazolidinone intermediate and its conversion into the iminium carboxylate isomer.

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More information

e-pub ahead of print date: 22 December 2009
Published date: 25 January 2010
Keywords: aldol reaction, nonlinear effects, organocatalysis, proline, thiourea
Organisations: Chemistry

Identifiers

Local EPrints ID: 347711
URI: http://eprints.soton.ac.uk/id/eprint/347711
ISSN: 0947-6539
PURE UUID: 0b525a16-0979-455e-8726-4f00aed88d3a
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

Catalogue record

Date deposited: 29 Jan 2013 11:54
Last modified: 17 Dec 2019 01:38

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