Events The 13th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

This submission belongs to the session a. General Organic Synthesis of the event The 13th International Electronic Conference on Synthetic Organic Chemistry

Published date

31 Oct, 2009

Citation

Christian Rolando, Didier Barbry, Maël Penhoat, Dual Proline/Water Compatible Lewis Acid Activation: a Biomimetic Approach for Direct Asymmetric Aldol Reaction, in Proceedings of The 13th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2009, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-13-00193

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Dual Proline/Water Compatible Lewis Acid Activation: a Biomimetic Approach for Direct Asymmetric Aldol Reaction

Christian Rolando ¹

Didier Barbry ¹

Maël Penhoat ¹

1. Laboratoire de Chimie Organique et Macromoléculaire UMR8009, Université de Lille 1, Sciences et Technologies – 59655 Villeneuve d’Ascq, France

Abstract

A novel approach based on combinations of various water compatible Lewis acids and L-proline cocatalysts has been evaluated for the direct asymmetric aldol reaction. From this screening zinc (II) chloride salts lead to the highest stereoselectivities. Optimized catalytic conditions (Catalytic system : L-proline : 20 (percent) / ZnCl2 : 10 (percent) - Solvent mixture : DMSO/H2O – 8 : 2) give anti aldol product with improved enantioselectivity (>99 (percent) e.e.) compared to a moderately stereoselective procedure based on proline activation only.

Keywords

Utilization of piperazine for interphase catalytic systems

Highly turnover number cyanosilylation of carbonyl compounds catalyzed by tetraethylammonium 2- (hydroxycarbamoyl)benzoate as a bifunctional organocatalyst: The role of hydrogen bonding