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Cyclodextrin Ketones with the Catalytic Group at the Secondary Rim and Their Effectiveness in Enzyme‐Like Epoxidation of Stilbenes
Author(s) -
Fenger Thomas Hauch,
Marinescu Lavinia G.,
Bols Mikael
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001696
Subject(s) - chemistry , cyclodextrin , ketone , catalysis , styrene , styrene oxide , nitro , medicinal chemistry , organic chemistry , oxide , copolymer , polymer , alkyl
Several new cyclodextrin ketones with a ketone attached to the secondary face of the cyclodextrin in the form of a 2,3‐ O ‐(2‐oxopropane‐1,3‐diyl) or 2‐oxo group are reported. These compounds and a selection of known cyclodextrin ketones having the ketone at the primary face were investigated as epoxidation catalysts for oxidation of stilbenes and styrene. A method for determination of k cat in these epoxidations is presented, which was used to determine the rate accelerations for the cyclodextrin ketones relative to background reaction. The highest rate acceleration obtained for epoxidation of 4‐methoxy‐4′‐nitro‐ trans ‐stilbene was 221. The highest enantioselectivity obtained was 76 % ee of ( S )‐styrene oxide.