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Increased structural complexity leads to higher activity: peptides as efficient and versatile catalysts for asymmetric aldol reactions 总被引:3,自引:0,他引:3
[reaction: see text] Peptides containing a secondary amine and a carboxylic acid in a specific orientation to each other are presented as highly efficient catalysts for asymmetric aldol reactions: (1) their activity is considerably higher compared to that of proline, and (2) the enantioselectivity of the peptidic catalysts can be changed from (R)- to (S)-selectivity by simple modifications of the secondary structure. 相似文献
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Dr. Leo D. M. Nicholls Prof. Helma Wennemers 《Chemistry (Weinheim an der Bergstrasse, Germany)》2021,27(70):17559-17564
The combination of a peptide catalyst and a gold catalyst is presented for enantioselective addition reactions between branched aldehydes and allenamides. The two catalysts act in concert to provide γ,δ-enamide aldehydes bearing a fully substituted, benzylic stereogenic center – a structural motif common in many natural products and therapeutically active compounds – with good yields and enantioselectivities. The reaction tolerates a variety of alkyl and alkoxy substituted aldehydes and the products can be elaborated into several chiral building blocks bearing either 1,4- or 1,5- functional group relationships. Mechanistic studies showed that the conformational features of the peptide are important for both the catalytic efficiency and stereochemistry, while a balance of acid/base additives is key for ensuring formation of the desired product over undesired side reactions. 相似文献
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Wennemers H 《Chemical communications (Cambridge, England)》2011,47(44):12036-12041
Over the past decade several peptides have been developed as effective asymmetric catalysts for a range of synthetically useful reactions. Many have properties that are difficult to achieve with other catalysts. The article highlights features that render peptidic organocatalysts unique and attractive for future applications. Challenges such as the design of peptidic catalysts are discussed. 相似文献