title: Cyclopropene derivatives as precursors to enantioenriched cyclopropanols and n-butenals possessing quaternary carbon stereocenters.
abstract: The diastereoselective carbocupration reaction of cyclopropenylmethyl ethers followed by addition of oxenoid leads to the formation of diastereo- and enantiomerically enriched 2,2,3,3-tetrasubstituted cyclopropanol derivatives. Ring fragmentation of the copper cyclopropanolate leads to acyclic butenal derivatives possessing enantiomerically enriched α-quaternary carbon stereocenters in a single-pot operation.
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, Technion City, Haifa 32000 (Israel).
authors.forename: Marwan
authors.initials: M
authors.lastname: Simaan
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, Technion City, Haifa 32000 (Israel).
authors.forename: Pierre-Olivier
authors.initials: PO
authors.lastname: Delaye
authors.affiliation: State Key Laboratory of Organometallic Chemistry. Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Lu, Shanghai, 200032 (China).
authors.forename: Min
authors.initials: M
authors.lastname: Shi
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, Technion City, Haifa 32000 (Israel). chilanm@tx.technion.ac.il.
authors.forename: Ilan
authors.initials: I
authors.lastname: Marek
keywords: copper; metalation; small-ring systems; strained molecules; synthetic methods