Nonheme Iron-Catalyzed Enantioselective cis -Dihydroxylation of Aliphatic Acrylates as Mimics of Rieske Dioxygenases

Abstract

Open AccessCCS ChemistryRESEARCH ARTICLE17 Feb 2022Nonheme Iron-Catalyzed Enantioselective cis-Dihydroxylation of Aliphatic Acrylates as Mimics of Rieske Dioxygenases Jie Chen, Xiu Luo, Ying Sun, Si Si, Yuankai Xu, Yong-Min Lee, Wonwoo Nam and Bin Wang Jie Chen Google Scholar More articles by this author , Xiu Luo Google Scholar More articles by this author , Ying Sun Google Scholar More articles by this author , Si Si Google Scholar More articles by this author , Yuankai Xu Google Scholar More articles by this author , Yong-Min Lee Google Scholar More articles by this author , Wonwoo Nam Google Scholar More articles by this author and Bin Wang Google Scholar More articles by this author https://doi.org/10.31635/ccschem.022.202101780 SectionsSupplemental MaterialAboutPDF ToolsAdd to favoritesTrack Citations ShareFacebookTwitterLinked InEmail 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 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 from the competitive epoxidation, cis-dihydroxylation and overoxidation reactions. Herein, we disclose a biologically inspired nonheme iron complex-catalyzed enantioselective cis-dihydroxylation of multi-substituted acrylates using hydrogen peroxide (H2O2) as a terminal oxidant by controlling the non-ligating or weakly ligating counterions of iron(II) complexes; we have demonstrated a dramatic counteranion effect on the enantioselective cis-dihydroxylation of olefins by H2O2 catalyzed by nonheme iron complexes. A range of structurally disparate alkenes are 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 and the ubiquity and synthetic utility of enantioenriched syn-2,3-dihydroxy esters in pharmaceuticals candidates and natural products, we expect that this strategy to some extent can serve as a promising compliment to the well-known Sharpless asymmetric dihydroxylation. Download figure Download PowerPoint Next article FiguresReferencesRelatedDetails Issue AssignmentNot Yet AssignedSupporting Information Copyright & Permissions© 2022 Chinese Chemical Society Downloaded 0 times Loading ...