Interfacing microbial styrene production with a biocompatible cyclopropanation reaction.

Chiral Imidazoles and Imidazole N-Oxides as Ligands for Stereoselective Cyclopropanation reactions

New, optically active ligands derived from imidazole were tested in the cyclopropanation reaction of styrene using ethyl diazoacetate and copper(I) triflate as a catalyst. DOI: https://doi.org/10.2174/157017812800221735 Posted at the Zurich Open Repository and Archive, University of Zurich ZORA URL: https://doi.org/10.5167/uzh-61481 Accepted Version Originally published at: Mloston, G; Mucha, P...

Non-natural olefin cyclopropanation catalyzed by diverse cytochrome P450s and other hemoproteins.

Recent work has shown that engineered variants of cytochrome P450BM3 (CYP102A1) efficiently catalyze non-natural reactions, including carbene and nitrene transfer reactions. Given the broad substrate range of natural P450 enzymes, we set out to explore if this diversity could be leveraged to generate a broad panel of new catalysts for olefin cyclopropanation (i.e., carbene transfer). Here, we t...

Palladium(II) carboxylates and palladium(I) carbonyl carboxylate complexes as catalysts for olefin cyclopropanation with ethyl diazoacetate.

Palladium(I) carbonyl carboxylate complexes [Pd(mu-CO)(mu-RCO2)](n) (R = Me, n = 4; R = CMe(3), n = 6) and the corresponding palladium(II) carboxylates (acetate and pivalate) catalyze the cyclopropanation of olefins with ethyl diazoacetate. The performance of these catalysts is similar in terms of selectivity and cyclopropane yields, regardless of the oxidation state of the metal center. Howeve...

Towards Semisynthetic Bioorganometallic Protein Catalysts: Cyclopropanation of Styrene with Ruthenium(II)-Modified Porphyrin Cofactors in Aqueous Solution

A flexible and versatile strategy for the covalent immobilization of chiral catalysts based on pyridinebis(oxazoline) ligands.

[reaction: see text] Flexible and versatile methods have been developed for the immobilization of chiral pyridinebis(oxazoline) ligands by covalent bonding to a solid support, either by grafting or by polymerization. Different spacers can easily be introduced to modulate the support-ligand distance and the electronic properties of the chiral ligand. As an example, 2,6-bis[(S)-4-isopropyloxazoli...