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

Niama Ei-Hamdouni; Xavier Companyó; Ramon Rios; Albert Moyano

doi:10.1002/chem.200902678

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

Niama Ei-Hamdouni
, Xavier Companyó
, Ramon Rios
, Albert Moyano

Chemistry

Research output: Contribution to journal › Article › peer-review

90 Scopus citations

Abstract

"Figure Presented" It's an affair of four: The study of nonlinear effects in the proline-thioureacatalyzed 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.

Original language	British English
Pages (from-to)	1142-1148
Number of pages	7
Journal	Chemistry - A European Journal
Volume	16
Issue number	4
DOIs	https://doi.org/10.1002/chem.200902678
State	Published - 2010

Keywords

Aldol reaction
Nonlinear effects
Organocatalysis
Proline, thiourea

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10.1002/chem.200902678

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AU - Ei-Hamdouni, Niama

AU - Companyó, Xavier

AU - Rios, Ramon

AU - Moyano, Albert

PY - 2010

Y1 - 2010

N2 - "Figure Presented" It's an affair of four: The study of nonlinear effects in the proline-thioureacatalyzed 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.

AB - "Figure Presented" It's an affair of four: The study of nonlinear effects in the proline-thioureacatalyzed 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.

KW - Aldol reaction

KW - Nonlinear effects

KW - Organocatalysis

KW - Proline, thiourea

UR - https://www.scopus.com/pages/publications/76549131001

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JF - Chemistry - A European Journal

IS - 4

ER -

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

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Keywords

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