Chiral Bioinspired Non-Heme Iron Complexes for Enantioselective Epoxidation of α,β-Unsaturated Ketones

✍ Scribed by Mei Wu; Cheng-Xia Miao; Shoufeng Wang; Xiaoxue Hu; Chungu Xia; Fritz E. Kühn; Wei Sun

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 381 KB
• Volume: 353
• Category: Article
• ISSN: 1615-4150
• DOI: 10.1002/adsc.201100267

✦ Synopsis

Chiral bioinspired iron complexes of N 4 ligands based on the ethylenediamine backbone display remarkable levels of enantioselectivity for the first time in the asymmetric epoxidation of a,b-unsaturated ketones using hydrogen peroxide (up to 87% ee) or peracetic acid as oxidant, respectively. Notablely, isotopic labeling with H 2 18 O strongly demonstrated that there is a reversible water binding step prior to generation of the significant intermediate.

usually derived from the decay of the LFe(IV)=O species or thermodynamic sinks for a number of iron complexes was identified by HR-MS. In addition, the possible mechanisms were proposed and LFe(V)=O species may be the main active intermediate in the catalytic system.