Literature DB >> 16018665

Cycloisomerization of dienes with carbophilic lewis acids: mimicking terpene biosynthesis with Pt(II) catalysts.

William D Kerber1, Michel R Gagné.   

Abstract

[reaction: see text]. Dicationic Pt(II) complexes containing triphosphine pincer ligands are excellent catalysts for the cycloisomerization of 1,6- and 1,7-dienes into bicyclopropane carbocycles. In analogy to the biosynthetic route to these monoterpene-like compounds, carbocation intermediates are proposed and supported by trapping experiments. Reactivation of the trapped intermediates indicates that cation generation by C-C bond formation is both rapid and reversible.

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Year:  2005        PMID： 16018665      PMCID： PMC2515936          DOI： 10.1021/ol051277c

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  12 in total

1.  Coordinated olefins as incipient carbocations: catalytic codimerization of ethylene and internal olefins by a dicationic Pt(II)-ethylene complex.

Authors:  Christine Hahn; Maria E Cucciolito; Aldo Vitagliano
Journal:  J Am Chem Soc       Date:  2002-08-07       Impact factor: 15.419

2.  Cationic gold(I) complexes: highly alkynophilic catalysts for the exo- and endo-cyclization of enynes.

Authors:  Cristina Nieto-Oberhuber; M Paz Muñoz; Elena Buñuel; Cristina Nevado; Diego J Cárdenas; Antonio M Echavarren
Journal:  Angew Chem Int Ed Engl       Date:  2004-04-26       Impact factor: 15.336

3.  Allylic lithium oxyanionic directed and facilitated simmons-smith cyclopropanation: stereoselective synthesis of (+/-)-cis-sabinene hydrate and a novel ring expansion.

Authors:  D Cheng; T Kreethadumrongdat; T Cohen
Journal:  Org Lett       Date:  2001-06-28       Impact factor: 6.005

4.  Catalytic isomerization of 1,5-enynes to bicyclo[3.1.0]hexenes.

Authors:  Michael R Luzung; Jordan P Markham; F Dean Toste
Journal:  J Am Chem Soc       Date:  2004-09-08       Impact factor: 15.419

5.  PtCl2-catalyzed cycloisomerizations of 5-en-1-yn-3-ol systems.

Authors:  Youssef Harrak; Christophe Blaszykowski; Matthieu Bernard; Kevin Cariou; Emily Mainetti; Virginie Mouriès; Anne-Lise Dhimane; Louis Fensterbank; Max Malacria
Journal:  J Am Chem Soc       Date:  2004-07-21       Impact factor: 15.419

6.  Platinum- and gold-catalyzed cycloisomerization reactions of hydroxylated enynes.

Authors:  Victor Mamane; Tobias Gress; Helga Krause; Alois Fürstner
Journal:  J Am Chem Soc       Date:  2004-07-21       Impact factor: 15.419

7.  Intramolecular cyclopropanation of unsaturated terminal epoxides.

Authors:  David M Hodgson; Ying Kit Chung; Jean-Marc Paris
Journal:  J Am Chem Soc       Date:  2004-07-21       Impact factor: 15.419

8.  Pd(II)- and Pt(II)-mediated polycyclization reactions of 1,5- and 1,6-dienes: evidence in support of carbocation intermediates.

Authors:  Jeong Hwan Koh; Michel R Gagné
Journal:  Angew Chem Int Ed Engl       Date:  2004-06-28       Impact factor: 15.336

9.  Stereochemistry of cyclopropane formation involving group IV organometallic complexes.

Authors:  Charles P Casey; Neil A Strotman
Journal:  J Am Chem Soc       Date:  2004-02-18       Impact factor: 15.419

10.  Functionalized carbo- and heterocycles via Pt-catalyzed asymmetric alkoxycyclization of 1,6-enynes.

Authors:  Lise Charruault; Véronique Michelet; Rossana Taras; Serafino Gladiali; Jean-Pierre Genêt
Journal:  Chem Commun (Camb)       Date:  2004-02-27       Impact factor: 6.222
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  10 in total

1.  Asymmetric oxidative cation/olefin cyclization of polyenes: evidence for reversible cascade cyclization.

Authors:  Charles A Mullen; Alison N Campbell; Michel R Gagné
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

2.  Carbonium vs. carbenium ion-like transition state geometries for carbocation cyclization - how strain associated with bridging affects 5-exo vs. 6-endo selectivity.

Authors:  Osvaldo Gutierrez; Jason G Harrison; Ryan J Felix; Fernando Cortés Guzman; Michel R Gagné; Dean J Tantillo
Journal:  Chem Sci       Date:  2013-10       Impact factor: 9.825

3.  Terminating platinum-initiated cation-olefin reactions with simple alkenes.

Authors:  Joseph G Sokol; Chandra Sekhar Korapala; Peter S White; Jennifer J Becker; Michel R Gagné
Journal:  Angew Chem Int Ed Engl       Date:  2011-05-13       Impact factor: 15.336

4.  Steric Crowding Makes Challenging C(sp3)-F Reductive Eliminations Feasible.

Authors:  Shu-Bin Zhao; Jennifer J Becker; Michel R Gagné
Journal:  Organometallics       Date:  2011-08-08       Impact factor: 3.876

5.  Computational Studies on the Pt(II)-Catalyzed Cycloisomerization of 1,6-dienes into Bicyclopropanes: A Mechanistic Quandary Evaluated by DFT.

Authors:  Franziska Bell; Jason Holland; Jennifer C Green; Michel R Gagné
Journal:  Organometallics       Date:  2009-04-13       Impact factor: 3.876

6.  Catalytic enantioselective cyclization and C3-fluorination of polyenes.

Authors:  Nikki A Cochrane; Ha Nguyen; Michel R Gagne
Journal:  J Am Chem Soc       Date:  2013-01-08       Impact factor: 15.419

7.  Reversibility effects on the stereoselectivity of Pt(II)-mediated cascade poly-ene cyclizations.

Authors:  Jeremiah A Feducia; Michel R Gagné
Journal:  J Am Chem Soc       Date:  2007-12-21       Impact factor: 15.419

8.  Promoting C-C Bond Coupling of Benzyne and Methyl Ligands in Electron-Deficient (triphos)Pt-CH3+ Complexes.

Authors:  Marzieh Dadkhah Aseman; Christina A Roselli; Michel R Gagné
Journal:  Organometallics       Date:  2015-06-02       Impact factor: 3.876

9.  Gold-catalyzed enantioselective ring-expanding cycloisomerization of cyclopropylidene bearing 1,5-enynes.

Authors:  Hongchao Zheng; Ryan J Felix; Michel R Gagné
Journal:  Org Lett       Date:  2014-03-31       Impact factor: 6.005

10.  Electrophilic Pt(II) complexes: precision instruments for the initiation of transformations mediated by the cation-olefin reaction.

Authors:  Ryan J Felix; Colleen Munro-Leighton; Michel R Gagné
Journal:  Acc Chem Res       Date:  2014-05-20       Impact factor: 22.384
  10 in total

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