title: Atom-economical synthesis of functionalized cycloalkanes via catalytic redox cycloisomerization of propargyl alcohols.
abstract: An atom-economical procedure for the direct synthesis of cycloalkanes from propargyl alcohols is reported. This high-yielding one-pot process involves a sequence consisting of a Ru-catalyzed redox isomerization of ynols into enones or an enal followed by an intramolecular Michael addition of a variety of carbon nucleophiles. Furthermore, an asymmetric variant of this protocol realized by the aid of a chiral nonracemic diamine catalyst, which provides the cyclization products in up to 97% ee, is presented.
authors.affiliation: Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu
authors.forename: Barry M
authors.initials: BM
authors.lastname: Trost
authors.forename: Alexander
authors.initials: A
authors.lastname: Breder
authors.forename: Bao
authors.initials: B
authors.lastname: Kai
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D003516:Cycloparaffins / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D020005:Propanols / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry
chemical_list: D000480:Alkynes; D003516:Cycloparaffins; D020005:Propanols; D012428:Ruthenium; C028255:propargyl alcohol