Tripeptides as Efficient Asymmetric Catalysts for 1,4-Addition Reactions of Aldehydes to Nitroolefins-A Rational Approach

摘要

Peptides have become increasingly popular as asymmetric catalysts for a range of reactions. Features such as facile synthesis, modularity, and often high selectivity and activity render peptidic catalysts attractive alternatives to metal-based catalysts and other organocatalysts. One of the largest challenges in the development of peptidic catalysts is the prediction and incorporation of desirable catalytic properties into a given peptide. This is already a challenge for small rigid organocatalysts, but even more so for short peptidic catalysts bearing many more degrees of rotational freedom. As a result, combinatorial chemistry has proven to be a valuable tool for the identification of peptidic catalysts. In this study we used insight gained from conformational analysis to guide the development of tripeptides as efficient asymmetric catalysts for conjugate addition reactions of aldehydes to nitroolefins.