Highly Efficient Alkene Epoxidation and Aziridination Catalyzed by Iron(II) Salt + 4,4′,4′′-Trichloro-2,2′:6′,2′′-terpyridine/4,4′′-Dichloro-4′- O -PEG-OCH 3 -2,2′:6′,2′′-terpyridine

Department of Chemistry and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The University of Hong Kong, Pokfulam Road, Hong Kong, China.
Organic Letters (Impact Factor: 6.36). 07/2008; 10(15):3275-8. DOI: 10.1021/ol801157m
Source: PubMed


"Iron(II) salt + 4,4',4''-trichloro-2,2':6',2''-terpyridine" is an effective catalyst for epoxidation and aziridination of alkenes and intramolecular amidation of sulfamate esters. The epoxidation of allylic-substituted cycloalkenes achieved excellent diastereoselectivities up to 90%. ESI-MS results supported the formation of iron-oxo and -imido intermediates. Derivitization of Cl 3terpy to O-PEG-OCH 3-Cl 2terpy renders the terpyridine unit to be recyclable, and the "iron(II) salt + 4,4''-dichloro-4'- O-PEG-OCH 3-2,2':6',2''-terpyridine" protocol can be reused without a significant loss of catalytic activity in the alkene epoxidation.

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