title: Lewis acid-catalyzed conjugate additions of silyloxyallenes: a selective solution to the intermolecular Rauhut-Currier problem.
abstract: Silyloxyallenes serve as highly useful alpha-acylvinyl anion equivalents. These latent allenolates undergo conjugate additions to alkylidene malonates in the presence of 10 mol % Sc(OTf) 3. The reaction delivers intermolecular Rauhut-Currier products in excellent yields and regioselectivities for a wide scope of substrates. Notably, the formal cross-coupling of two different alpha,beta-unsaturated carbonyl compounds (a cross Rauhut-Currier reaction) is achieved. Preliminary investigations have demonstrated good levels of enantioselectivity for the addition of a racemic silyloxyallene with a chiral Lewis acid.
authors.affiliation: Department of Chemistry, Northwestern University, Evanston, IL 60208, USA.
authors.forename: Troy E
authors.initials: TE
authors.lastname: Reynolds
authors.forename: Michael S
authors.initials: MS
authors.lastname: Binkley
authors.forename: Karl A
authors.initials: KA
authors.lastname: Scheidt
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D007202:Indicators and Reagents; D008314:Malonates / Q000737:chemistry; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D007202:Indicators and Reagents; D008314:Malonates; D017646:Organosilicon Compounds