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• W2010903885 abstract "The use of protonated l-prolinethioamide instead of the free base derivative 1 as the organocatalyst for the direct aldol addition has a profound and appreciable effect on both the yield and the stereochemical course of the reaction. 4-Nitrobenzaldehyde (2) reacts with acetone in the presence of the protonated catalyst 1·TFA, affording aldol product 3 with a yield up to 99% and an ee up to 98%. The catalyst loading can be lowered to 2.5 mol %. More than 20 different acids were investigated as an additive, and its role as cocatalyst has been discussed. Furthermore, reactions of l-prolinethioamide salts with acetone have been monitored using ESI-MS and 1H NMR techniques, giving insight into the mechanism of the direct aldol reaction. The presumed formation of the iminium salt 10 has been unambiguously confirmed." @default.
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• W2010903885 date "2007-01-10" @default.
• W2010903885 modified "2023-09-29" @default.
• W2010903885 title "Brønsted Acids as Additives for the Direct Asymmetric Aldol Reaction Catalyzed by <scp>l</scp>-Prolinethioamides. Direct Evidence for Enamine−Iminium Catalysis" @default.
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• W2010903885 doi "https://doi.org/10.1021/jo062149k" @default.
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