title: Cascade Mn-Mediated γ-Alkylation/oxa-Michael Addition of Enones with 1,3-Dicarbonyls.
abstract: A radical-based strategy for regioselective γ-C-C bond formation/oxa-conjugate addition, forming the tetrahydrobenzofuran core common to many bioactive natural products is described. The technique utilizes readily available enone derivatives and 1,3-dicarbonyl compounds as coupling partners in an oxidative formal [3+2] cycloaddition mediated by Mn(III) . The transformation delivers polycyclic products in good yields and proceeds with complete regiocontrol and excellent stereoselectivity. Sterically encumbered substrates are notably well-tolerated and bond formation occurs readily to form neopentyl and all-carbon quaternary centers in good yields. Several stereo- and chemoselective transformations of the products are described.
authors.affiliation: Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois, 60607, USA.
authors.forename: Xiaoguang
authors.initials: X
authors.lastname: Liu
authors.affiliation: Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois, 60607, USA.
authors.forename: Xiaohong
authors.initials: X
authors.lastname: Chen
authors.affiliation: Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois, 60607, USA. jtmohr@uic.edu.
authors.forename: Justin T
authors.identifier: http://orcid.org/0000-0002-7005-3322
authors.initials: JT
authors.lastname: Mohr
keywords: manganese; oxidation; radicals; regioselectivity; stereoselectivity