Premium
A Double Conformationally Restricted Dynamic Supramolecular System for the Substrate‐Selective Epoxidation of Olefins—A Comparative Study on the Influence of Preorganization
Author(s) -
Lindbäck Emil,
Cherraben Sawsen,
Francoïa JeanPatrick,
Sheibani Esmaeil,
Lukowski Bartosz,
Proñ Agnieszka,
NorouziArasi Hassan,
Månsson Kristoffer,
Bujalowski Pawel,
Cederbalk Anna,
Pham Thanh Huong,
Wixe Torbjörn,
Dawaigher Sami,
Wärnmark Kenneth
Publication year - 2015
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201402726
Subject(s) - substrate (aquarium) , supramolecular chemistry , catalysis , chemistry , selectivity , supramolecular catalysis , stereochemistry , combinatorial chemistry , double bond , crystallography , polymer chemistry , crystal structure , organic chemistry , oceanography , geology
A double conformationally restricted kinetically labile supramolecular catalytic system, the third generation, was designed and synthesized. We investigated the substrate selectivity of this system by performing competitive pairwise epoxidations of pyridyl‐ and phenyl‐appended olefins. We compared the obtained substrate selectivities to previous less preorganized generations of this system. Five different substrate pairs were investigated, and the present double conformationally restricted system showed higher normalized substrate selectivities (pyridyl versus phenyl) for two of the substrate pairs than the previous less conformationally restricted generations. As for the preorganization of the components of the system, the catalyst, and the receptor part, it was shown that for each substrate pair there was one generation that was better than the other to generate substrate‐selective catalysis.