First Evidence of Proline Acting as a Bifunctional Catalyst in the Baylis–Hillman Reaction Between Alkyl Vinyl Ketones and Aryl Aldehydes

6533b86efe1ef96bd12cb56a

RESEARCH PRODUCT

First Evidence of Proline Acting as a Bifunctional Catalyst in the Baylis–Hillman Reaction Between Alkyl Vinyl Ketones and Aryl Aldehydes

Renato Noto Adriana Mossuto Marculescu Serena Riela Michelangelo Gruttadauria Francesco Giacalone Paolo Lo Meo

subject

chemistry.chemical_classification Ketone Proline Aldehyde Aryl Organic Chemistry Semi-empiricalcalculation Settore CHIM/06 - Chimica Organica Bifunctional catalyst Catalysis Organocatalysi chemistry.chemical_compound chemistry Organocatalysis Organic chemistry Amine gas treating Baylis–Hillman reaction Physical and Theoretical Chemistry Baylis–Hillman reaction Bifunctional Reaction mechanism

description

Proline in the presence of sodium hydrogen carbonate has been found to be an effective catalyst for the Baylis–Hillman reaction between methyl or ethyl vinyl ketone and aryl aldehydes. Screening of several amine catalysts showed that an ionizable carboxylic function directly linked to the secondary amine catalyst plays an important role in the synthesis of the desired product in good yield. The data obtained has allowed us to suggest, for the first time, that proline, sarcosine, pipecolinic acid and homoproline may act as bifunctional catalysts via a bicyclic enaminolactone species as intermediate. Quantum-mechanical calculations (PM3/COSMO and ab initio 3-21G/COSMO) support this mechanism and give more insight into the role of hydrogen carbonate.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

year	journal	country	edition	language
2008-03-01	European Journal of Organic Chemistry

https://doi.org/10.1002/ejoc.200701112

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