View : 335 Download: 0
Nonheme Iron-Catalyzed Enantioselective cis-Dihydroxylation of Aliphatic Acrylates as Mimics of Rieske Dioxygenases
- Title
- Nonheme Iron-Catalyzed Enantioselective cis-Dihydroxylation of Aliphatic Acrylates as Mimics of Rieske Dioxygenases
- Authors
- Chen J.; Luo X.; Sun Y.; Si S.; Xu Y.; Lee Y.-M.; Nam W.; Wang B.
- Ewha Authors
- 남원우; 이용민
- SCOPUS Author ID
- 남원우; 이용민
- Issue Date
- 2022
- Journal Title
- CCS Chemistry
- ISSN
- 2096-5745
- Citation
- CCS Chemistry vol. 4, no. 7, pp. 2369 - 2381
- Keywords
- bioinspired catalysis; cis-dihydroxylation; nonheme iron catalyst; Rieske dioxygenase; tetradentate nitrogen-donor ligand
- Publisher
- Chinese Chemical Society
- Indexed
- SCOPUS
- Document Type
- Article
- Abstract
- Enantioselective cis-dihydroxylation of alkenes represents an ideal route to synthesize enantioenriched syn-2,3-dihydroxy esters that are important structural motifs in numerous biologically and pharmaceutically relevant molecules. Bioinspired nonheme iron-catalyzed enantioselective cis-dihydroxylation meets the requirement of the modern synthetic chemistry from the atomic economy, green chemistry, and sustainable development perspectives. However, nonheme iron-catalyzed enantioselective cis-dihydroxylation is much underdeveloped because of the formidable challenges of controlling chemo- and enantioselectivities and product selectivity caused by the competitive epoxidation, cis-dihydroxylation, and overoxidation reactions. Herein, we disclose the fabrication of a biologically inspired nonheme iron complex-catalyzed enantioselective cis-dihydroxylation of multisubstituted acrylates using hydrogen peroxide (H2O2) as the terminal oxidant by controlling the non-ligating or weakly ligating counterions of iron(II) complexes, demonstrating a dramatic counteranion effect on the enantioselective cis-dihydroxylation of olefins by H2O2 catalyzed by nonheme iron complexes. A range of structurally disparate alkenes were transformed to the corresponding syn-2,3-dihydroxy esters in practically useful yields with exquisite chemo- and enantioselectivities (up to 99% ee). Given the mild and benign nature of this biologically inspired oxidation system as well as the ubiquity and synthetic utility of enantioenriched syn-2,3-dihydroxy esters as pharmaceuticals candidates and natural products, we expect that this strategy could serve as a promising complement to the well-known Sharpless asymmetric dihydroxylation, which is the chemical reaction of an alkene with OsO4 to produce a vicinal diol. © CCS Chemistry.All right reserved.
- DOI
- 10.31635/ccschem.022.202201780
- Appears in Collections:
- 자연과학대학 > 화학·나노과학전공 > Journal papers
- Files in This Item:
There are no files associated with this item.
- Export
- RIS (EndNote)
- XLS (Excel)
- XML