J. Am. Chem. Soc., Just Accepted Manuscript
DOI: 10.1021/jacs.5b12681
Publication Date (Web): January 22, 2016
Copyright © 2016 American Chemical Society
1 QBIS Research Group, Institut de Química Computacional i Catàlisi (IQCC) and Departament de Química, Uni‐
versitat de Girona, Campus Montilivi, Girona E‐17071, Catalonia, Spain.
2 Organic Chemistry & Catalysis, Debye Institute for Nanomaterials Science, Utrecht University. Universiteitsweg
99, 3584 CG Utrecht, The Netherlands.
http://pubs.acs.org/doi/abs/10.1021/jacs.5b12681
Abstract
An iron complex with a C1-symmetric tetradentate N-based ligand catalyze the asymmetric epoxidation of cyclic enones and cyclohexene ketones with aqueous hydrogen peroxide, providing the corresponding epoxides in good to excellent yields and enantioselectivities (up to 99 % yield, and 95 % ee), under mild conditions and in short reaction times. Evidence is provided that reactions involve an electrophilic oxidant, and this element is employed in performing site selective epoxidation of enones containing two alkene sites
This is the first example of highly enantioselective(>90% ee ) epoxidation of non aromatic substrate with iron catalyst and enantioselective electrophilic oxidation of this challenging class of substrates.
The design of C1 symmetric complex where the electoronic and steric properties of distinct heterocycles are combined constitutes a novel aspect.
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