title: Copper phosphoramidite catalyzed enantioselective ring-opening of oxabicyclic alkenes: remarkable reversal of stereocontrol.
abstract: [reaction: see text] An unprecedented copper phosphoramidite catalyzed enantioselective alkylative ring-opening reaction of oxabenzonorbornadiene derivatives with dialkylzinc reagents is reported. The reaction shows high levels of anti-stereoselectivity (up to anti/syn >99:1), complementary to the Pd(0)-catalyzed syn-selective ring-opening protocol, allowing a new entry to anti-dihydronaphthols with high enantioselectivity (up to 99% ee).
authors.affiliation: Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, The Netherlands.
authors.forename: Fabio
authors.initials: F
authors.lastname: Bertozzi
authors.forename: Mauro
authors.initials: M
authors.lastname: Pineschi
authors.forename: Franco
authors.initials: F
authors.lastname: Macchia
authors.forename: Leggy A
authors.initials: LA
authors.lastname: Arnold
authors.forename: Adriaan J
authors.initials: AJ
authors.lastname: Minnaard
authors.forename: Ben L
authors.initials: BL
authors.lastname: Feringa