title: Donor-Acceptor Cyclopropanes as 1,2-Dipoles in GaCl3-Mediated [4 + 2]-Annulation with Alkenes: Easy Access to the Tetralin Skeleton.
abstract: A new process for (4 + 2)-annulation of donor-acceptor cyclopropanes (DACs) with unsaturated compounds in the presence of anhydrous GaCl3 has been developed. In this process, DACs act as sources of formal 1,2- and 1,4-dipoles to give polysubstituted tetralins in high yields and with high regio- and diastereoselectivity. Alkenes with both aryl and alkyl substituents at the double bond undergo this reaction equally readily. A most likely mechanism of the reaction has been proposed. It involves preliminary generation of a key 1,2-dipolar gallium complex and its subsequent participation in annulation with an alkene.
authors.affiliation: †N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospekt, 119991 Moscow, Russian Federation.|‡V. A. Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, 32 Vavilov Street, 119991 Moscow, Russian Federation.
authors.forename: Roman A
authors.initials: RA
authors.lastname: Novikov
authors.affiliation: †N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospekt, 119991 Moscow, Russian Federation.
authors.forename: Anna V
authors.initials: AV
authors.lastname: Tarasova
authors.affiliation: †N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospekt, 119991 Moscow, Russian Federation.
authors.forename: Victor A
authors.initials: VA
authors.lastname: Korolev
authors.affiliation: †N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospekt, 119991 Moscow, Russian Federation.
authors.forename: Evgeny V
authors.initials: EV
authors.lastname: Shulishov
authors.affiliation: ‡V. A. Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, 32 Vavilov Street, 119991 Moscow, Russian Federation.
authors.forename: Vladimir P
authors.initials: VP
authors.lastname: Timofeev
authors.affiliation: †N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospekt, 119991 Moscow, Russian Federation.
authors.forename: Yury V
authors.initials: YV
authors.lastname: Tomilov
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D061565:Cycloaddition Reaction; D003521:Cyclopropanes / Q000737:chemistry*; D005708:Gallium / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013764:Tetrahydronaphthalenes / Q000737:chemistry*
chemical_list: D000475:Alkenes; D003521:Cyclopropanes; D013764:Tetrahydronaphthalenes; C034163:gallium chloride; D005708:Gallium