Search

Transition metal‐catalyzed, C−C and C−N bond‐forming reactions have made an enormous impact in the way complex molecules are assembled. The benefits of solid‐phase chemistry soon made this type of reaction applicable to solid‐supported processes. In this review, we report the most recent applications and possibilities of this combination. Remarkably, the solid‐phase CuAAC and ring‐closing metathesis have demonstrated an important role in synthetic biology, alike more traditional Pd‐catalyzed reactions, such as Suzuki‐Miyaura, Heck, Sonogashira, which are valuable tools for accessing libraries of biologically relevant small molecules. Examples proved the validity of solid‐phase transition metal‐catalyzed reactions as a practical and fast strategy to cover the current organic chemistry demands. [ABSTRACT FROM AUTHOR]

Olefin metathesis constitutes a seemingly endless area of research that has had an enormous impact on several branches of chemistry, both in industry and in academia. Once the potential of this reaction as a carbon-carbon bond-forming tool was widely recognized, its adaptation to solid-phase chemistry naturally followed. This review documents the applications and possibilities that polymer-bound alkenes have provided in the challenging cross-version of olefin metathesis, through efforts that are far from exhausted. [ABSTRACT FROM AUTHOR]

Solid-phase synthetic strategies toward the generation of libraries of biologically relevant molecules were developed using olefin cross-metathesis as a key step. It is remarkably the formal 9 alkane metathesis based on a one-pot, microwave-assisted, ruthenium-catalyzed cross-metathesis and reduction to obtain Csp³ - Csp³ linkages. [ABSTRACT FROM AUTHOR]

We have developed a study on the factors that influence the intrasite interactions in the cross-metathesis on solid support. When such interactions are possible, the outcome of the intrasite by-product depends on the non-immobilized olefin and the precatalyst used. The comparatively poor reactivity of first generation Grubbs precatalyst makes the easier intrasite coupling to succeed. [ABSTRACT FROM AUTHOR]

An efficient and stereoselective procedure for a rapid access to diverse trans 3-alkyl β-lactams by solid-phase methodology is described. [Copyright &y& Elsevier]

The polymer-supported Staudinger reaction proceeded smoothly under mild conditions to give the corresponding β-lactams in good to high overall yields with excellent cis-selectivity. Upon applying this reaction system, an efficient asymmetric synthesis of β-lactams was accomplished, when chiral acid chlorides or chiral aldehydes were used. These optically active β-lactams would be useful precursors for the generation of combinatorial libraries of potential antibiotics and enzyme inhibitors. [Copyright &y& Elsevier]

Abstract: An efficient and versatile methodology for the preparation of valuable triazolyl aminoacyl (peptidyl) penicillins is described. Solid-phase Cu(I)-catalyzed Hüisgen 1,3-dipolar cycloaddition was used as the key step showing general applicability and excellent regioselectivity either with CuI or [Cu(CH3CN)4]PF6 as Cu(I) source. [Copyright &y& Elsevier]

A synthetic strategy has been developed for the preparation of immobilized 1,2-aminoalcohols starting from easily available and renewable chiral building blocks. They were tested as chiral ligands for the asymmetric diethylzinc addition to carbonyl compounds. Enantioselectivities were comparable to those observed for non-immobilized analogs. These results provide strong evidence for the flexibility of our approach to generate highly valuable supported chiral ligands derived from cellulose-rich materials. [ABSTRACT FROM AUTHOR]

Abstract: An efficient protocol for the rapid generation of libraries of biologically promising β-lactams is described. Key step is a solid-phase based multicomponent Petasis reaction. [Copyright &y& Elsevier]

Abstract: A straightforward solid phase-based strategy for the rapid generation of two small libraries of trans 3-alkyl-substituted β-lactams is described. For the glycine-derived library, a controlled excess of nonactivated acid chlorides was used to prevent oxazinone formation. The second library involved the attachment of Fmoc-protected p-aminophenol to Wang resin for the preparation of structurally-closed analogues of known cholesterol absorption inhibitors. This strategy allowed us to introduce diversity in the three variable positions of the β-lactam ring. [Copyright &y& Elsevier]