Abstract
Multicomponent and multicatalytic reactions are those processes that try to imitate the way the enzymatic machinery transforms simple building blocks into complex products. The development of asymmetric versions of these reactions is a step forward in our dream of mirroring the exquisite selectivity of biological processes. In this context, the present work describes a new reaction for the asymmetric synthesis of furo[2,3-b]pyrrole derivatives from simple 3-butynamines, glyoxylic acid and anilines in the presence of a dual catalytic system, formed from a gold complex and a chiral phosphoric acid. Computations, aimed to understand the exceptional performance of 9-anthracenyl-substituted BINOL-derived phosphoric acid catalyst, suggest a fundamental role of non-covalent interactions being established between the catalyst and the reagents for the outcome of the multicomponent process. The linear geometry of the anthracenyl substituent along with the presence of an electron-withdrawing group in the aniline and an aromatic substituent in the 3-butynamine derivative seem to be key structural factors to explain the experimental results and, particularly, the high stereoselectivity.
Highlights
IntroductionWithout question, a major subject of modern chemistry. In traditional catalytic strategies, a single catalyst interacts with a reagent lowering the energetic barrier of the subsequent reaction with another reagent
Catalysis has become, without question, a major subject of modern chemistry
Once we had veri ed that the 9-anthracenyl-substituted BINOL-derived phosphoric acid CPAF was an optimal acid catalyst to perform the desired asymmetric multicomponent and multicatalytic process, we addressed the scope of the transformation
Summary
Without question, a major subject of modern chemistry. In traditional catalytic strategies, a single catalyst interacts with a reagent lowering the energetic barrier of the subsequent reaction with another reagent. This strategy has delivered vast numbers of new reactions over many decades, new directions in the eld of catalysis are necessary in order to address the demands of sustainability and global wellbeing of our society In this context, multicatalytic reactions (one-pot catalysis), de ned as those processes where several reactions occur in a single ask as a result of the action of multiple catalyst, have become a powerful synthetic tool.[1] On the other hand, multicomponent reactions, which are those processes where several starting materials react together to yield a product that retains the majority of atoms of the reactants, have become of signi cant interest in the eld of organic synthesis.[2] As a result of merging both tools, multicomponent and multicatalytic reactions have recently emerged as one of those new concepts in the area of catalysis.[3] In these processes, three or more starting materials react by means of two or more catalysts (all present from the onset of the reaction) to produce structurally and functionally complex products (Scheme 1a). The exquisite stereoselectivity of biosynthetic reactions is difficult to imitate and the development of asymmetric multicomponent and multicatalytic reactions remains challenging.[4]
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