title: Diastereospecific nazarov cyclization of fully substituted dienones: generation of vicinal all-carbon-atom quaternary stereocenters.
abstract: No vacancy: Fully substituted dienones that are highly polarized by a vinylogous carbonate group were found to undergo a remarkably rapid and diastereospecific Nazarov cyclization that led to cyclopentenones with vicinal all-carbon-atom quaternary centers (see example; SEM=2-(trimethylsilyl)ethoxymethyl, Tf=trifluoromethanesulfonyl).
authors.affiliation: Chemistry Department, University of Hawaii at Manoa, 2545 The Mall, Honolulu, HI 96822 (USA).
authors.forename: Anais
authors.initials: A
authors.lastname: Jolit
authors.forename: Saleta
authors.initials: S
authors.lastname: Vazquez-Rodriguez
authors.forename: Glenn P A
authors.initials: GP
authors.lastname: Yap
authors.forename: Marcus A
authors.initials: MA
authors.lastname: Tius
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis*; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D003517:Cyclopentanes; D007659:Ketones
keywords: Nazarov cyclization; diastereoselectivity; quaternary stereocenters; rearrangement; synthetic methods