Iridium(III)-bis(imidazolinyl)phenyl catalysts for enantioselective C-H functionalization with ethyl diazoacetate

• Type of Material: Article
• Authors: N. Mace Weldy, Emory University; A. G. Schafer, Emory University; C.P. Owens, Emory University; C.J. Herting, Emory University; A. Varela-Alvarez, Emory University; S. Chen, Emory University; Z. Niemeyer, University of Utah; Jamal Musaev, Emory University; M.S. Sigman, University of Utah; Huw Davies, Emory University; Simon Blakey, Emory University
• Language: English
• Date: 2016-01-01
• Publisher: Royal Society of Chemistry: Open Access
• Publication Version: Final Published Version
• Copyright Statement: © 2016 The Royal Society of Chemistry.
• License: Creative Commons Attribution 3.0 Unported
• Final Published Version (URL): http://dx.doi.org/10.1039/c6sc00190d
• Title of Journal or Parent Work: Chemical Science
• ISSN: 2041-6520
• Volume: 7
• Issue: 5
• Start Page: 3142
• End Page: 3146
• Grant/Funding Information: This research was supported by the National Science Foundation under the Center for Chemical Innovation in Selective C–H Functionalization (CHE1205646).
• Keywords: CYCLOPROPANATION; Science & Technology; RHODIUM; Chemistry; NATURAL-PRODUCTS; CARBENOIDS; COMPLEXES; Physical Sciences; LIGANDS; Chemistry, Multidisciplinary; BOND ACTIVATION; INSERTION
• Research Categories: Chemistry, General

Abstract

The intermolecular enantioselective C-H functionalization with acceptor-only metallocarbenes is reported using a new family of Ir(iii)-bis(imidazolinyl)phenyl catalysts, developed based on the interplay of experimental and computational insights. The reaction is tolerant of a variety of diazoacetate precursors and is found to be heavily influenced by the steric and electronic properties of the substrate. Phthalan and dihydrofuran derivatives are functionalized in good yields and excellent enantioselectivities.