Substrate-Dependent Nonlinear Effects in Proline-Thiourea-Catalyzed Aldol Reactions: Unraveling the Role of the Thiourea Co-Catalyst

It's an affair of four: 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 See...

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Published inChemistry : a European journal Vol. 16; no. 4; pp. 1142 - 1148
Main Authors El-Hamdouni, Niama, Companyó, Xavier, Rios, Ramon, Moyano, Albert
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 25.01.2010
WILEY‐VCH Verlag
Wiley Subscription Services, Inc
Subjects
Acetone - chemistry
aldol reaction
Benzaldehydes - chemistry
Catalysis
Chemistry
Hydrogen Bonding
Magnetic Resonance Spectroscopy
nonlinear effects
organocatalysis
Oxazolidinones - chemistry
proline
Proline - chemistry
Spectrometry, Mass, Electrospray Ionization
Substrate Specificity
thiourea
Thiourea - chemistry
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Summary:It's an affair of four: 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.
Bibliography:Spanish Ministry of Science and Education - No. AYA2006-15648-C02-01
ark:/67375/WNG-P74CKDK5-5
Spanish Ministry of Foreign Affairs and Cooperation
istex:99BBE12F5FC4EA9BB222D88DFE2F432ED6CF58A2
ArticleID:CHEM200902678
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.200902678