Aza(oxa)bicyclo[3.2.0]heptenes are accessed through the PtCl2 -catalyzed cycloisomerizations of heteroatom-tethered 1,6-enynes featuring a terminal alkyne and amide as the solvent. It is shown that the weak coordinating properties of the solvent and alkyl substituent(s) at the propargylic carbon atom favor the formation of cyclobutenes instead of other possible cycloisomerization products such as 1,3-diene derivatives or cyclopropane-fused heterocycles.
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Cyclobutene formation in PtCl2-catalyzed cycloisomerizations of heteroatom-tethered 1,6-enynes.
Chemistry
September 2014
Aix-Marseille Université, Centrale Marseille, CNRS, ISm2, UMR 7313, 13397 Marseille (France).
Aza(oxa)bicyclo[3.2.0]heptenes are accessed through the PtCl2 -catalyzed cycloisomerizations of heteroatom-tethered 1,6-enynes featuring a terminal alkyne and amide as the solvent.
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Beilstein J Org Chem
August 2012
Laboratoire Charles Friedel, UMR 7223, Ecole Nationale Supérieure de Chimie de Paris, Chimie ParisTech, 11 rue P. et M. Curie, F-75231 Paris Cedex 05, France.
A comprehensive study on the asymmetric gold-catalyzed cycloisomerization reaction of heteroatom tethered 1,6-enynes is described. The cycloisomerization reactions were conducted in the presence of the chiral cationic Au(I) catalyst consisting of (R)-4-MeO-3,5-(t-Bu)(2)-MeOBIPHEP-(AuCl)(2) complex and silver salts (AgOTf or AgNTf(2)) in toluene under mild conditions to afford functionalized bicyclo[4.1.
View Article and Find Full Text PDFAsymmetric Au(i)-catalyzed synthesis of bicyclo[4.1.0]heptene derivatives via a cycloisomerization process of 1,6-enynes.
Chem Commun (Camb)
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Laboratoire Charles Friedel, Ecole Nationale Supérieure de Chimie de Paris UMR 7223, 11 rue P. et M. Curie, F-75231 Paris Cedex 05, France.
The enantioselective asymmetric gold-catalyzed cycloisomerization reactions of heteroatom tethered 1,6-enynes are conducted in the presence of a chiral cationic Au(i) catalyst ((R)-4-MeO-3,5-(t-Bu)(2)-MeOBIPHEP-(AuCl)(2)/AgOTf system) in toluene under mild conditions and lead to functionalized bicyclo[4.1.0]heptene derivatives in excellent enantiomeric excesses ranging from 90-98%.
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J Org Chem
November 2004
Sección de Síntesis Orgánica e Imagen Molecular por Resonancia Magnética, Instituto Universitario de Investigación, UNED, c/Senda del Rey 9, Madrid 28040, Spain.
A mechanistic study based on DFT theoretical calculations for the PtCl(2)-catalyzed formation of bicyclic adducts from heteroatom tethered 1,6-enynes is reported. Different reaction pathways have been taken into account and the results are discussed. This analysis clearly reveals that the kinetically preferred pathway involves an initial 6-endo-cyclization from a triggered reactant complex by pi-complexation of Pt(II) onto the alkyne to form a cyclopropyl platina-carbene intermediate, followed by a [1,2]-hydrogen shift.
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