Developing selective polymerizations from complex monomer mixtures is an important challenge. Here, dinuclear catalysts allow selective polymerization from mixtures of sterically hindered tricyclic anhydrides, carbon dioxide and epoxides to yield well-controlled copoly(ester-carbonates). Surprisingly, two very similar homogeneous catalysts differing only in the central metal, zinc versus magnes...

Sulfone-substituted γ- and δ-lactams have been prepared in a single step with high diastereoselectivity. Sulfonylglutaric anhydrides produce intermediates that readily decarboxylate to provide δ-lactams with high diastereoselectivity. Substituents at the 3- or 4-position of the glutaric anhydride induce high levels of stereocontrol. Sulfonylsuccinic anhydrides produce intermediate carboxylic ac...

We report a new synthetic methodology for poly(ester amide)s by anionic ring-opening copolymerization of N-sulfonyl aziridines and cyclic anhydrides. Phosphazenes organocatalysts have been found to promote highly-active, controlled, selective alternating in the absence any competitive side reaction (zwitterionic mechanism exchange transacylations). Mechanistic studies shown first-order dependen...

In this study, renewable products with potentially interesting properties and applications were synthesized by functionalizing linseed oil via epoxidation epoxy ring-opening carboxylic acids anhydrides. LDHs (Layered Double Hydroxides), a well-known class of materials used for wide range reactions, are the catalysts in overall advantages facile separation reusability. our different types anhydr...

A Pd-catalyzed regioselective C-H bond carbonylation of N-alkyl anilines for the synthesis of isatoic anhydrides has been developed. The key Pd-catalyst intermediate has been isolated and characterized. This novel Pd-catalyzed carbonylation reaction tolerates a wide range of functional groups and is a reliable method for the rapid elaboration of readily available N-alkyl anilines into a variety...

Complementary to enantioselective transformations of planar functionalities, catalytic desymmetrization of meso compounds is another fundamentally important strategy for asymmetric synthesis. However, experimentally established stereochemical models on how a chiral catalyst discriminates between two enantiotopic functional groups in the desymmetrization of a meso substrate are particularly lack...

5(4H)-Oxazolones can be formed through the activation of acylated α-amino acids or of peptide C termini. They constitute potentially activated intermediates in the abiotic chemistry of peptides that preceded the origin of life or early stages of biology and are capable of yielding mixed carboxylic-phosphoric anhydrides upon reaction with phosphate esters and nucleotides. Here, we present the re...

Aminoacyl adenylates (aa-AMPs) constitute essential intermediates of protein biosynthesis. Their polymerization in aqueous solution has often been claimed as a potential route to abiotic peptides in spite of a highly efficient CO2-promoted pathway of hydrolysis. Here we investigate the efficiency and relevance of this frequently overlooked pathway from model amino acid phosphate mixed anhydride...

An efficient and odourless procedure for a one-pot synthesis of thioesters by the reaction of benzoic anhydrides, thiourea and various organic halides (primary, allylic, and benzylic) or structurally diverse, electron-deficient alkenes (ketones, esters, and nitriles) in the presence of Et3N has been developed. In this method, thiobenzoic acids were in situ generated from the reaction of thioure...