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Pure Appl. Chem., 1992, Vol. 64, No. 3, pp. 387-392

http://dx.doi.org/10.1351/pac199264030387

Stereochemical aspects on the formation of chiral allenes from propargylic ethers and epoxides

A. Alexakis

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  • Campolo Damien, Arif Tanzeel, Borie Cyril, Mouysset Dominique, Vanthuyne Nicolas, Naubron Jean-Valère, Bertrand Michèle P., Nechab Malek: Double Transfer of Chirality in Organocopper-Mediated bis(Alkylating) Cycloisomerization of Enediynes. Angew. Chem. 2014, 126, 3291. <http://dx.doi.org/10.1002/ange.201310530>
  • Campolo Damien, Arif Tanzeel, Borie Cyril, Mouysset Dominique, Vanthuyne Nicolas, Naubron Jean-Valère, Bertrand Michèle P., Nechab Malek: Double Transfer of Chirality in Organocopper-Mediated bis(Alkylating) Cycloisomerization of Enediynes. Angew. Chem. Int. Ed. 2014, 53, 3227. <http://dx.doi.org/10.1002/anie.201310530>
  • Collins Beatrice S. L., Suero Marcos G., Gaunt Matthew J.: Copper-Catalyzed Arylative Meyer-Schuster Rearrangement of Propargylic Alcohols to Complex Enones Using Diaryliodonium Salts. Angew. Chem. 2013, 125, 5911. <http://dx.doi.org/10.1002/ange.201301529>
  • Collins Beatrice S. L., Suero Marcos G., Gaunt Matthew J.: Copper-Catalyzed Arylative Meyer-Schuster Rearrangement of Propargylic Alcohols to Complex Enones Using Diaryliodonium Salts. Angew. Chem. Int. Ed. 2013, 52, 5799. <http://dx.doi.org/10.1002/anie.201301529>
  • Denichoux Aurélien, Debien Laurent, Cyklinsky Mathieu, Kaci Malika, Chemla Fabrice, Ferreira Franck, Pérez-Luna Alejandro: Three-Carbon Homologation of Diorganozincs with Lithiated Acetylenic Epoxides. J. Org. Chem. 2013, 78, 134. <http://dx.doi.org/10.1021/jo302128n>
  • Yang Mingyu, Yokokawa Natsumi, Ohmiya Hirohisa, Sawamura Masaya: Synthesis of Conjugated Allenes through Copper-Catalyzed γ-Selective and Stereospecific Coupling between Propargylic Phosphates and Aryl- or Alkenylboronates. Org Lett 2012, 14, 816. <http://dx.doi.org/10.1021/ol2033465>
  • Reeker Helene, Norrby Per-Ola, Krause Norbert: Mechanistic Studies of the CuH-Catalyzed Synthesis of α-Hydroxyallenes. Organometallics 2012, 31, 8024. <http://dx.doi.org/10.1021/om3007129>
  • Ohmiya Hirohisa, Yokobori Umi, Makida Yusuke, Sawamura Masaya: General Approach to Allenes through Copper-Catalyzed γ-Selective and Stereospecific Coupling between Propargylic Phosphates and Alkylboranes. Org Lett 2011, 13, 6312. <http://dx.doi.org/10.1021/ol202866h>
  • ALEXAKIS A.: ChemInform Abstract: Stereochemical Aspects on the Formation of Chiral Allenes from Propargylic Ethers and Epoxides. ChemInform 2010, 23, no. <http://dx.doi.org/10.1002/chin.199232284>
  • Krause Norbert, Aksin-Artok Özge, Breker Viola, Deutsch Carl, Gockel Birgit, Poonoth Manojkumar, Sawama Yoshinari, Sawama Yuka, Sun Tao, Winter Christian: Combined coinage metal catalysis for the synthesis of bioactive molecules. Pure and App Chemis 2010, 1. <http://dx.doi.org/10.1351/PAC-CON-09-09-23>
  • Tang Xiaoping, Woodward Simon, Krause Norbert: Synthesis of α-Hydroxyallenes by Copper-Catalyzed SN2′ Substitution of Propargylic Dioxolanones. Eur J Org Chem 2009, 2009, 2836. <http://dx.doi.org/10.1002/ejoc.200900226>
  • García Ruano José Luis, Marcos Vanesa, Alemán José: Configurational Control of Benzyl Carbanion-Copper Complexes by Sulfinyl Groups: Synthesis of Optically Pure Allenes with Central and Axial Chirality. Angew. Chem. 2008, 120, 6942. <http://dx.doi.org/10.1002/ange.200802158>
  • García Ruano José Luis, Marcos Vanesa, Alemán José: Configurational Control of Benzyl Carbanion-Copper Complexes by Sulfinyl Groups: Synthesis of Optically Pure Allenes with Central and Axial Chirality. Angew Chem Int Ed 2008, 47, 6836. <http://dx.doi.org/10.1002/anie.200802158>
  • Deutsch Carl, Lipshutz Bruce H., Krause Norbert: Klein aber effizient: Kupferhydrid-katalysierte Synthese von α-Hydroxyallenen. Angew Chem 2007, 119, 1677. <http://dx.doi.org/10.1002/ange.200603739>
  • Deutsch Carl, Lipshutz Bruce H., Krause Norbert: Small but Effective: Copper Hydride Catalyzed Synthesis of α-Hydroxyallenes. Angew Chem Int Ed 2007, 46, 1650. <http://dx.doi.org/10.1002/anie.200603739>
  • Jansen Axel, Krause Norbert: Exceptional reactivity and selectivity of lower-order cyanocuprates in the SN2′-substitution of propargyl acetates. Inorg Chim Ada 2006, 359, 1761. <http://dx.doi.org/10.1016/j.ica.2005.06.045>
  • Riveiros Ricardo, Rodríguez David, Pérez Sestelo José, Sarandeses Luis A.: Palladium-Catalyzed Cross-Coupling Reaction of Triorganoindium Reagents with Propargylic Esters. Org Lett 2006, 8, 1403. <http://dx.doi.org/10.1021/ol060192o>
  • Sano Shigeki, Shimizu Hisashi, Kim Kweon, Lee Woo Song, Shiro Motoo, Nagao Yoshimitsu: Expeditious Syntheses of Conjugated Allenyl Esters and Oxazoles through a Cascade Reaction of α-Alkynyl Malonates under Alkaline Conditions. Chem Pharm Bull 2006, 54, 196. <http://dx.doi.org/10.1248/cpb.54.196>
  • Okamoto Sentaro, Tominaga Satoshi, Saino Naoko, Kase Kouki, Shimoda Kentaro: Allylic substitution reactions with Grignard reagents catalyzed by imidazolium and 4,5-dihydroimidazolium carbene–CuCl complexes. J Organomet Chem 2005, 690, 6001. <http://dx.doi.org/10.1016/j.jorganchem.2005.07.096>
  • Krause Norbert, Hoffmann-Röder Anja: Synthesis of allenes with organometallic reagents. Tetrahedron 2004, 60, 11671. <http://dx.doi.org/10.1016/j.tet.2004.09.094>
  • Imada Yasushi, Ueno Katsuya, Kutsuwa Koji, Murahashi Shun-Ichi: Palladium-Catalyzed Asymmetric Alkylation of 2,3-Alkadienyl Phosphates. Synthesis of Optically Active 2-(2,3-Alkadienyl)malonates. Chem Lett 2002, 140. <http://dx.doi.org/10.1246/cl.2002.140>
  • Mikami Koichi, Yoshida Akihiro: Regio- and enantioselective synthesis of allenic esters by samarium(II)-mediated reduction of propargylic compounds through dynamic kinetic protonation. Tetrahedron 2001, 57, 889. <http://dx.doi.org/10.1016/S0040-4020(00)01044-9>
  • Krause Norbert, Purpura Martin: „Remote Stereocontrol“ in der Organokupferchemie: hoch enantioselektive Synthese von Vinylallenen durch 1,5-Substitution von Eninacetaten. Angew Chem 2000, 112, 4512. <http://dx.doi.org/10.1002/1521-3757(20001201)112:23<4512::AID-ANGE4512>3.0.CO;2-5>
  • Krause Norbert, Purpura Martin: “Remote Stereocontrol” in Organocopper Chemistry: Highly Enantioselective Synthesis of Vinylallenes by 1,5-Substitution of Enyne Acetates. Angew Chem 2000, 39, 4355. <http://dx.doi.org/10.1002/1521-3773(20001201)39:23<4355::AID-ANIE4355>3.0.CO;2-C>
  • Spino Claude, Fréchette Sylvie: Synthesis of non-racemic unsymmetrical tetrasubstituted vinylallenes. Tetrahetron Lett 2000, 41, 8033. <http://dx.doi.org/10.1016/S0040-4039(00)01406-4>
  • Purpura Martin, Krause Norbert: Regio- and Stereoselective Synthesis of Vinylallenes by 1,5-(SN′′)-Substitution of Enyne Acetates and Oxiranes with Organocuprates. Eur J Org Chem 1999, 1999, 267. <http://dx.doi.org/10.1002/(SICI)1099-0690(199901)1999:1<267::AID-EJOC267>3.0.CO;2-V>
  • Okamoto Sentaro, An Duk Keun, Sato Fumie: Synthesis of optically active allenyltitaniums having axial chirality by the reaction of optically active propargylic compounds with a reagent. Tetrahetron Lett 1998, 39, 4551. <http://dx.doi.org/10.1016/S0040-4039(98)00829-6>
  • Chemla Fabrice, Bernard Nicolas, Normant Jean F.: Lewis acid-mediated ring opening of propargylic epoxides: A stereospecific synthesis of 1,2-disubstituted homopropargylic alcohols. Tetrahetron Lett 1998, 39, 6715. <http://dx.doi.org/10.1016/S0040-4039(98)01433-6>
  • Krause Norbert, Gerold Andreas: Regio- und stereoselektive Synthesen mit Organokupferreagentien. Angew Chem 1997, 109, 194. <http://dx.doi.org/10.1002/ange.19971090304>
  • Mikami Koichi, Yoshida Akihiro: Dynamisch-kinetische Protonierung von racemischen Allenylmetallverbindungen zur asymmetrischen Synthese von Allencarbonsäureestern. Angew Chem 1997, 109, 892. <http://dx.doi.org/10.1002/ange.19971090819>
  • Baldoli Clara, Del Buttero Paola, Licandro Emanuela, Maiorana Stefano, Papagni Antonio, Torchio Maurizio: Stereoselective alkynylation of chiral benzaldehyde chromium tricarbonyl complexes. Synthesis of optically active alkynyl alcohols. Tetrahetron Lett 1993, 34, 7943. <http://dx.doi.org/10.1016/S0040-4039(00)61518-6>
  • Handke Gabriele, Krause Norbert: Diastereoselective 1,6-addition reactions of organocuprates to chiral 5-alkynylidene-1,3-dioxan-4-ones. Tetrahetron Lett 1993, 34, 6037. <http://dx.doi.org/10.1016/S0040-4039(00)61721-5>