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Pure Appl. Chem., 2006, Vol. 78, No. 2, pp. 197-208

http://dx.doi.org/10.1351/pac200678020197

Transition-metal-catalyzed reactions of allenes

Shengming Ma

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China and Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang, China

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  • Xia Xiao-Feng, Wang Yu-Qi, Zhang Lu-Lu, Song Xian-Rong, Liu Xue-Yuan, Liang Yong-Min: Palladium-Catalyzed CH Activation and Intermolecular Annulation with Allenes. Chem. Eur. J. 2014, n/a. <http://dx.doi.org/10.1002/chem.201304300>
  • Soriano Elena, Fernández Israel: Allenes and computational chemistry: from bonding situations to reaction mechanisms. Chem. Soc. Rev. 2014, 43, 3041. <http://dx.doi.org/10.1039/c3cs60457h>
  • Weatherly Cale D., Guzei Ilia A., Schomaker Jennifer M.: Stereocontrolled Synthesis of 1,3-Diamino-2-ols by Aminohydroxylation of Bicyclic Methylene-Aziridines. Eur. J. Org. Chem. 2013, 2013, 3667. <http://dx.doi.org/10.1002/ejoc.201300416>
  • Hawkins Alison, Jakubec Pavol, Ironmonger Alan, Dixon Darren J.: An expedient stereoselective route to the ACE tricyclic core of manzamine A via a palladium-catalysed arylative allene spirocyclisation cascade. Tetrahedron Letters 2013, 54, 365. <http://dx.doi.org/10.1016/j.tetlet.2012.10.111>
  • Xie Xi, Ma Shengming: Palladium-catalyzed asymmetric coupling cyclization of terminal γ-allenols with aryl iodides. Chem. Commun. 2013, 49, 5693. <http://dx.doi.org/10.1039/c3cc40892b>
  • Wang Honggen, Glorius Frank: Milde Rhodium(III)-katalysierte C-H-Aktivierung und intermolekulare Anellierung mit Allenen. Angew. Chem. 2012, 124, 7430. <http://dx.doi.org/10.1002/ange.201201273>
  • Wang Honggen, Glorius Frank: Mild Rhodium(III)-Catalyzed CH Activation and Intermolecular Annulation with Allenes. Angew. Chem. Int. Ed. 2012, 51, 7318. <http://dx.doi.org/10.1002/anie.201201273>
  • Adams Christopher S., Boralsky Luke A., Guzei Ilia A., Schomaker Jennifer M.: Modular Functionalization of Allenes to Aminated Stereotriads. J. Am. Chem. Soc. 2012, 134, 10807. <http://dx.doi.org/10.1021/ja304859w>
  • Boralsky Luke A., Hershberger John C., Marston Dagmara, Meis Alan R., Guzei Ilia A., Schomaker Jennifer M., Rigoli Jared W.: 1,4-Diazaspiro[2.2]pentanes as a Flexible Platform for the Synthesis of Diamine-Bearing Stereotriads. J Org Chern 2012, 120214071158007. <http://dx.doi.org/10.1021/jo3000282>
  • Weatherly Cale D., Rigoli Jared W., Schomaker Jennifer M.: Synthesis of 1,3-Diaminated Stereotriads via Rearrangement of 1,4-Diazaspiro[2.2]pentanes. Z Org Lett 2012, 14, 1704. <http://dx.doi.org/10.1021/ol300269u>
  • Okada Takuya, Shimoda Airi, Shinada Tetsuro, Sakaguchi Kazuhiko, Ohfune Yasufumi: Regioselective Prins Cyclization of Allenylsilanes. Stereoselective Formation of Multisubstituted Heterocyclic Compounds. Org. Lett. 2012, 14, 6130. <http://dx.doi.org/10.1021/ol302669q>
  • Hirano Masafumi, Okamoto Takuya, Komine Nobuyuki, Komiya Sanshiro: Stoichiometric Carbon–Carbon Bond Forming Reaction of 1,3-Diene with 1,2-Diene in a Ruthenium(0) Complex. Organometallics 2012, 31, 4639. <http://dx.doi.org/10.1021/om300326q>
  • Muñoz María Paz: Transition metal-catalysed intermolecular reaction of allenes with oxygen nucleophiles: a perspective. Biomol Chem 2012, 10, 3584. <http://dx.doi.org/10.1039/c2ob07128b>
  • Wan Baoqiang, Jia Guochen, Ma Shengming: Palladium-Catalyzed Highly Chemo-, Regio- and Stereoselective Synthesis of Eight- to Ten-Membered Lactones from Allenyl 3-Oxoalkanoates and Organic Halides. Synth Catal 2011, 353, 1763. <http://dx.doi.org/10.1002/adsc.201100075>
  • Aylward Miriam, Coeffard Vincent, Guiry Patrick J.: Palladium-Catalyzed Three-Component Transformation of Homoallenols: A Regio- and Stereoselective Route to 1,5-Amino Alcohols. J Org Chem 2011, 76, 3536. <http://dx.doi.org/10.1021/jo1025628>
  • Lim Yu-Na, Kim Hyo-Tong, Yoon Hyo-Sang, Jang Hye-Young: Regio- and Stereoselective Reductive Cyclization of 1,5-Bisallenes under Hydrogenation Conditions. Bull Kor Chem Soc 2011, 32, 3117. <http://dx.doi.org/10.5012/bkcs.2011.32.8.3117>
  • Fall Yacoub, Doucet Henri, Santelli Maurice: Arylation of alkenylidenecyclopropanes via Heck reaction. A simple access to arylallylidenecyclopropanes. Tetrahedron 2010, 66, 2181. <http://dx.doi.org/10.1016/j.tet.2010.01.052>
  • Guo Xun-Xiang, Sawano Takahiro, Nishimura Takahiro, Hayashi Tamio: Rhodium-catalyzed enantioselective alkynylative cyclization of allenyl aldehydes with terminal alkynes. Tet Asymm 2010, 21, 1730. <http://dx.doi.org/10.1016/j.tetasy.2010.04.039>
  • Poonoth Manojkumar, Krause Norbert: Stereoselective Synthesis of Conjugated Bisallenols as Precursors of Novel Bis(2,5-dihydrofuran) Derivatives. Adv Synth Catal 2009, 351, 117. <http://dx.doi.org/10.1002/adsc.200800469>
  • Shu Wei, Yu Qiong, Ma Shengming: Development of a New Spiro-BOX Ligand and Its Application in Highly Enantioselective Palladium-Catalyzed Cyclization of 2-Iodoanilines with Allenes. Adv Synth Catal 2009, 351, 2807. <http://dx.doi.org/10.1002/adsc.200900607>
  • Shu Wei, Jia Guochen, Ma Shengming: Palladium-Catalyzed Three-Component Cascade Cyclization Reaction of Bisallenes with Propargylic Carbonates and Organoboronic Acids: Efficient Construction of cis -Fused Bicyclo[4.3.0]nonenes. Angew. Chem. 2009, 121, 2826. <http://dx.doi.org/10.1002/ange.200805422>
  • Shu Wei, Jia Guochen, Ma Shengming: Palladium-Catalyzed Three-Component Cascade Cyclization Reaction of Bisallenes with Propargylic Carbonates and Organoboronic Acids: Efficient Construction of cis -Fused Bicyclo[4.3.0]nonenes. Angew. Chem. Int. Ed. 2009, 48, 2788. <http://dx.doi.org/10.1002/anie.200805422>
  • Broggini Gianluigi, Galli Simona, Rigamonti Micol, Sottocornola Silvia, Zecchi Gaetano: Entry to nitrogen-containing heterocycles by based-promoted heterocyclization on allenylamides of l-α-aminoacids. Tetrahetron Lett 2009, 50, 1447. <http://dx.doi.org/10.1016/j.tetlet.2009.01.074>
  • Antoniotti Sylvain, Duñach Elisabet: Tin(IV) triflimidate-catalyzed cyclization of epoxy esters to functionalized δ-hydroxy-γ-lactones. Tetrahetron Lett 2009, 50, 2536. <http://dx.doi.org/10.1016/j.tetlet.2009.03.055>
  • Yadav J.S., Subba Reddy B.V., Narasimhulu G., Purnima K.V.: FeCl3-catalyzed functionalization of monoterpenes via hydroalkylation of unactivated alkenes. Tetrahetron Lett 2009, 50, 5783. <http://dx.doi.org/10.1016/j.tetlet.2009.07.057>
  • Naka Hiroshi, Koseki Daiki, Kondo Yoshinori: Catalytic Deprotonative Functionalization of Propargyl Silyl Ethers with Imines. Adv Synth Catal 2008, 350, 1901. <http://dx.doi.org/10.1002/adsc.200800281>
  • Lian Xiongdong, Ma Shengming: An Efficient Approach to Substituted 1,5,7,8,9-Pentahydrocyclopenta[h]-2-Benzopyran-3-one Derivatives by a Palladium-Catalyzed Tandem Reaction of 2,7-Alkadiynylic Carbonates with 2,3-Allenoic Acids. Angew Chem 2008, 120, 8379. <http://dx.doi.org/10.1002/ange.200803424>
  • Lian Xiongdong, Ma Shengming: An Efficient Approach to Substituted 1,5,7,8,9-Pentahydrocyclopenta[h]-2-Benzopyran-3-one Derivatives by a Palladium-Catalyzed Tandem Reaction of 2,7-Alkadiynylic Carbonates with 2,3-Allenoic Acids. Angew Chem Int Ed 2008, 47, 8255. <http://dx.doi.org/10.1002/anie.200803424>
  • Löhr Sandra, Averbeck Jan, Schürmann Markus, Krause Norbert: Synthesis and Complexation Properties of Allenic Bipyridines, a New Class of Axially Chiral Ligands for Transition Metal Catalysis. Eur J Inorg Chem 2008, 2008, 552. <http://dx.doi.org/10.1002/ejic.200701049>
  • Sawama Yoshinari, Sawama Yuka, Krause Norbert: First total synthesis of (R,R,R)- and (3R,5S,9R)-bejarol by gold-catalyzed allene cycloisomerization and determination of absolute configuration of the natural product. Org Biomol Chem 2008, 6, 3573. <http://dx.doi.org/10.1039/b807733a>
  • Grau Fanny, Antoniotti Sylvain, Duñach Elisabet, Lemechko Pierre: Hydroalkoxylation of non-activated olefins catalysed by Lewis superacids in alcoholic solvents: an eco-friendly reaction. Tet Letts 2007, 48, 5731. <http://dx.doi.org/10.1016/j.tetlet.2007.06.102>
  • Ma Shengming: Transition Metal Catalyzed Reactions of Allenes. ChemInform 2006, 37. <http://dx.doi.org/10.1002/chin.200631278>