Michiel de Greef

Bio: Michiel de Greef is an academic researcher from University of Freiburg. The author has contributed to research in topics: Hydrocyanation & Planar chirality. The author has an hindex of 4, co-authored 5 publications receiving 979 citations. Previous affiliations of Michiel de Greef include VU University Amsterdam.

Recent Advances in Solution-Phase Multicomponent Methodology for the Synthesis of Heterocyclic Compounds

Abstract: Following the increased interest from the pharmaceutical industry for the generation of diverse libraries of heterocyclic compounds, scientific efforts have become more and more focused on the development of novel multi-component procedures as a means of gaining rapid access to such compounds. Initially, the development of solid-phase procedures received considerable attention. However, current efforts are increasingly concerned with the development of solution-phase procedures. The latter will be the subject of discussion in this review, which aims to give an overview of the progress made in the past decade. After a general introduction, non-catalyzed, acid-catalyzed, and transition metal-catalyzed solution-phase multi-component procedures for the preparation of a wide range of heterocycles will be discussed. The last chapter discusses the role of cycloaddition reactions in the development of novel MCRs for the synthesis of heterocyclic compounds. In spite of their important role in the synthesis of heterocyclic compounds, MCRs involving isocyanides are not discussed in this review, since the topic has been exhaustively reviewed several times. 1 Introduction 2 Non-Catalyzed MCRs 3 Acid-Catalyzed MCRs 4 Transition Metal-Catalyzed or -Mediated MCRs 5 MCRs Involving Cycloaddition Reactions 6 Conclusions and Outlook.

Recent Advances in Solution‐Phase Multicomponent Methodology for the Synthesis of Heterocyclic Compounds

Abstract: Following the increased interest from the pharmaceutical industry for the generation of diverse libraries of heterocyclic compounds, scientific efforts have become more and more focused on the development of novel multi-component procedures as a means of gaining rapid access to such compounds. Initially, the development of solid-phase procedures received considerable attention. However, current efforts are increasingly concerned with the development of solution-phase procedures. The latter will be the subject of discussion in this review, which aims to give an overview of the progress made in the past decade. After a general introduction, non-catalyzed, acid-catalyzed, and transition metal-catalyzed solution-phase multi-component procedures for the preparation of a wide range of heterocycles will be discussed. The last chapter discusses the role of cycloaddition reactions in the development of novel MCRs for the synthesis of heterocyclic compounds. In spite of their important role in the synthesis of heterocyclic compounds, MCRs involving isocyanides are not discussed in this review, since the topic has been exhaustively reviewed several times. 1 Introduction 2 Non-Catalyzed MCRs 3 Acid-Catalyzed MCRs 4 Transition Metal-Catalyzed or -Mediated MCRs 5 MCRs Involving Cycloaddition Reactions 6 Conclusions and Outlook.

Rapid combinatorial access to macrocyclic ansapeptoids and ansapeptides with natural-product-like core structures

Abstract: 14-Membered ansa-cyclopeptide alkaloids are among the most abundant natural macrocycles and thus valuable templates for diversity-oriented synthesis with biological relevance. A rapid synthesis of the core structure is conceivable by a combination of an Ugi four-component reaction with bifunctional building blocks to form the dipeptoid part, followed by a suitable macrocyclization reaction. The latter step is crucial, and an uncommon macroetherification gave the best results. The use of ammonium salts allows direct access to peptides instead of peptoids. Depending on the substitution pattern, some cyclopeptoids show planar chirality despite free rotation of the phenylene group. © Georg Thieme Verlag Stuttgart.

Chemistry and Biology Of Multicomponent Reactions

Abstract: Multicomponent reactions (MCRs) are one-pot reactions employing more than two starting materials, e.g. 3, 4, … 7, where most of the atoms of the starting materials are incorporated in the final product.1 Several descriptive tags are regularly attached to MCRs (Fig. 1): they are atom economic, e.g. the majority if not all of the atoms of the starting materials are incorporated in the product; they are efficient, e.g. they efficiently yield the product since the product is formed in one-step instead of multiple sequential steps; they are convergent, e.g. several starting materials combine in one reaction to form the product; they exhibit a very high bond-forming-index (BFI), e.g. several non-hydrogen atom bonds are formed in one synthetic transformation.2 Therefore MCRs are often a useful alternative to sequential multistep synthesis. Open in a separate window Figure 1 Above: multistep syntheses can be divergent (sequential) or convergent; below: in analogy MCR reactions are convergent and one or two component reactions are divergent or less convergent.

Asymmetric multicomponent reactions (amcrs): the new frontier

Abstract: Asymmetric multicomponent reactions involve the preparation of chiral compounds by the reaction of three or more reagents added simultaneously. This kind of addition and reaction has some advantages over classic divergent reaction strategies, such as lower costs, time, and energy, as well as environmentally friendlier aspects. All these advantages, together with the high level of stereoselectivity attained in some of these reactions, will force chemists in industry as in academia to adopt this new strategy of synthesis, or at least to consider it as a viable option. The positive aspects as well as the drawbacks of this strategy are discussed in this Review.

Multicomponent Reaction Design in the Quest for Molecular Complexity and Diversity

Abstract: Multicomponent reactions have become increasingly popular as tools for the rapid generation of small-molecule libraries. However, to ensure sufficient molecular diversity and complexity, there is a continuous need for novel reactions. Although serendipity has always played an important role in the discovery of novel (multicomponent) reactions, rational design strategies have become much more important over the past decade. In this Review, we present an overview of general strategies that allow the design of novel multicomponent reactions. The challenges and opportunities for the future will be discussed.