Effect of Additives on L-Proline Catalyzed Direct Asymmetric Aldol Reactions

doi:10.1016/S1872-2067(11)60394-X

Abstract

Abstract: The direct asymmetric aldol reaction of aromatic aldehydes with acetone catalyzed by L-proline was accelerated by the addition of diols or diphenols. The use of additives decrease the amount of L-proline needed and allowed the use of solvent free conditions. Catechol with two adjacent hydroxy groups on aromatic ring was the most efficient additive. Under the optimized conditions, 5 mol% L-proline with 1 mol% catechol gave excellent chiral selectivity (80% ee value) with > 90% yield, which was higher than that obtained using 30 mol% L-proline without an additive. Computations indicated that the additive promoted the reaction by an intermolecular hydrogen bond between the hydrogen of the hydroxyl group and the oxygen of the carbonyl group, which activated the carbonyl group of the aldehyde. Catechol with two adjacent hydroxyl groups on the aromatic ring can form two hydrogen bonds with the oxygen of the carbonyl group on the corresponding aldehyde. Therefore, the combination of L-proline and catechol was very efficient in catalyzing the direct asymmetric aldol reaction and gave a high yield in a short time.

Key words: L-proline, catechol, aromatic aldehyde, acetone, direct asymmetric aldol reaction, hydrogen bond interaction

LUO Jian-Qing, TAN Rong, KONG Yu, LI Cheng-Yong, YIN Dong-Hong. Effect of Additives on L-Proline Catalyzed Direct Asymmetric Aldol Reactions[J]. Chinese Journal of Catalysis, 2012, 33(7): 1133-1138.

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