title: Brook Rearrangement as a Trigger for the Ring Opening of Strained Carbocycles.
abstract: The combined regio- and stereoselective carbometalation of cyclopropenyl amides, followed by the addition of an acyl silane, led to the formation of polysubstituted cyclopropyl derivatives as unique diastereoisomers. Upon warming of the reaction mixture to room temperature, a Brook rearrangement proceeded with inversion of configuration to provide ready access to δ-ketoamides possessing a quaternary carbon center with high enantiomeric ratios through selective C-C bond cleavage of the ring.
authors.affiliation: The Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry and Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Haifa, 32000 (Israel).
authors.forename: Fa-Guang
authors.initials: FG
authors.lastname: Zhang
authors.affiliation: The Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry and Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Haifa, 32000 (Israel).
authors.forename: Guillaume
authors.initials: G
authors.lastname: Eppe
authors.affiliation: The Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry and Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Haifa, 32000 (Israel). chilanm@tx.technion.ac.il.
authors.forename: Ilan
authors.initials: I
authors.lastname: Marek
keywords: Brook rearrangement; one-pot reactions; quaternary carbon centers; strained molecules; synthetic methods