title: Stereoelectronic effect for the selectivity in C-H insertion of alkylidene carbenes and its application to the synthesis of platensimycin.
abstract: A systematic study of C-H insertion reactions with variously substituted and conformationally constrained substrates was carried out. High selectivity in the insertion between two competing C-H bonds caused by a strong stereoelectronic effect of an oxygen substituent was achieved. This regioselective C-H insertion reaction was employed as a platform to develop a concise asymmetric synthesis of platensimycin.
authors.affiliation: Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA.
authors.forename: Sang Young
authors.initials: SY
authors.lastname: Yun
authors.forename: Jun-Cheng
authors.initials: JC
authors.lastname: Zheng
authors.forename: Daesung
authors.initials: D
authors.lastname: Lee
mesh_terms: D000218:Adamantane / Q000138:chemical synthesis*; D000475:Alkenes / Q000737:chemistry*; D062365:Aminobenzoates / Q000138:chemical synthesis*; D000813:Anilides / Q000138:chemical synthesis*; D004987:Ethers / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D062365:Aminobenzoates; D000813:Anilides; D004987:Ethers; D007659:Ketones; C030011:carbene; D008697:Methane; D000218:Adamantane; C510909:platensimycin