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Pure Appl. Chem., 2002, Vol. 74, No. 1, pp. 175-180

http://dx.doi.org/10.1351/pac200274010175

Stereoselective syntheses of heterocycles via metallated alkoxyallenes

Hans-Ulrich Reissig, Wolfgang Schade, G. Marlyse Okala Amombo, Robert Pulz and Arndt Hausherr

Institut für Chemie ­ Organische Chemie, Freie Universität Berlin, Takustr. 3, D-14195 Berlin, Germany

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  • Wang Minyan, Fang Zhao, Fu Chunling, Ma Shengming: Metal Alkoxide Promoted Regio- and Stereoselective CO and CC Metathesis of Allenoates with Aldehydes. Angew. Chem. 2014, 126, 3278. <http://dx.doi.org/10.1002/ange.201310183>
  • Wang Minyan, Fang Zhao, Fu Chunling, Ma Shengming: Metal Alkoxide Promoted Regio- and Stereoselective CO and CC Metathesis of Allenoates with Aldehydes. Angew. Chem. Int. Ed. 2014, 53, 3214. <http://dx.doi.org/10.1002/anie.201310183>
  • Wang Zhenjun, Ren Jun, Wang Zhongwen: Lewis Acids Promoted Formal Intramolecular [3 + 2] Parallel and Cross-Cycloadditions of Cyclopropane 1,1-Diesters with Allenes. Org. Lett. 2013, 15, 5682. <http://dx.doi.org/10.1021/ol402662j>
  • Sun Peng-Shuai, Hu Jie, Wang Xiang-Chuan, Liu Lei, Liang Yong-Min: New light on an old reaction: phase-transfer-catalyzed intramolecular cyclization of propargyl compounds for synthesis of indene derivatives and disubstituted benzo[b]furans. Tetrahedron 2012, 68, 1367. <http://dx.doi.org/10.1016/j.tet.2011.12.055>
  • Alcaide Benito, Almendros Pedro: Novel Cyclization Reactions of Aminoallenes. Synth Catal 2011, 353, 2561. <http://dx.doi.org/10.1002/adsc.201100160>
  • Lechel Tilman, Gerhard Markus, Trawny Daniel, Brusilowskij Boris, Schefzig Luise, Zimmer Reinhold, Rabe Jürgen P., Lentz Dieter, Schalley Christoph A., Reissig Hans-Ulrich: Synthesis of 5-Acetyloxazoles and 1,2-Diketones from β-Alkoxy-β-ketoenamides and Their Subsequent Transformations. Chem Eur J 2011, 17, 7480. <http://dx.doi.org/10.1002/chem.201100382>
  • Alcaide Benito, Almendros Pedro: Allenyl-β-lactams: versatile scaffolds for the synthesis of heterocycles. Chem Record 2011, 11, 311. <http://dx.doi.org/10.1002/tcr.201100011>
  • Chen Guofei, Zhang Ya, Fu Chunling, Ma Shengming: A facile synthesis of β-allenyl furanimines via Pd-catalyzed cyclization of 2,3-allenamides with propargylic carbonates. Tetrahedron 2011, 67, 2332. <http://dx.doi.org/10.1016/j.tet.2011.01.041>
  • Bouché Léa, Reissig Hans-Ulrich: Synthesis of novel carbohydrate mimetics via 1,2-oxazines. PureAppl Chem 2011, 1. <http://dx.doi.org/10.1351/PAC-CON-11-09-20>
  • Lechel Tilman, Reissig Hans-Ulrich: New 5-Alkoxypyrimidine Derivatives from β-Alkoxy β-Keto Enamides and Ammonium Salts. Eur J Org Chem 2010, 2010, 2555. <http://dx.doi.org/10.1002/ejoc.201000056>
  • Alcaide Benito, Almendros Pedro, Aragoncillo Cristina: Exploiting [2+2] cycloaddition chemistry: achievements with allenes. Chem Soc Rev 2010, 39, 783. <http://dx.doi.org/10.1039/b913749a>
  • Pfrengle Fabian, Reissig Hans-Ulrich: Amino sugars and their mimetics via 1,2-oxazines. Chem Soc Rev 2010, 39, 549. <http://dx.doi.org/10.1039/b914356d>
  • Lechel Tilman, Dash Jyotirmayee, Eidamshaus Christian, Brüdgam Irene, Lentz Dieter, Reissig Hans-Ulrich: A three-component synthesis of β-alkoxy-β-keto-enamides—flexible precursors for 4-hydroxypyridine derivatives and their palladium-catalysed reactions. Org Biomol Chem 2010, 8, 3007. <http://dx.doi.org/10.1039/b925468d>
  • Chen Guofei, Jiang Xuefeng, Fu Chunling, Ma Shengming: The Diversified Reactivities of 1,5-Bisallenes. Chem Lett 2010, 39, 78. <http://dx.doi.org/10.1246/cl.2010.78>
  • Lechel Tilman, Reissig Hans-Ulrich: Synthesis of heterocycles via alkoxyallenes. Pure and App Chemis 2010, 1. <http://dx.doi.org/10.1351/PAC-CON-09-09-06>
  • Lechel Tilman, Lentz Dieter, Reissig Hans-Ulrich: Three-Component Synthesis of Highly Functionalized 5-Acetyloxazoles. Chem Eur J 2009, 15, 5432. <http://dx.doi.org/10.1002/chem.200900386>
  • C. Majumdar Krishna, Debnath Pradip, Roy Brindaban: Metal-Catalyzed Heterocyclization: Formation of Five- and Six-Membered Oxygen Heterocycles through Carbon-Oxygen Bond Forming Reactions. HETEROCYCLES 2009, 78, 2661. <http://dx.doi.org/10.3987/REV-09-656>
  • 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>
  • Deng Youqian, Li Jing, Ma Shengming: PdI2-Catalyzed Coupling–Cyclization Reactions Involving Two Different 2,3-Allenols: An Efficient Synthesis of 4-(1′,3′-Dien-2′-yl)-2,5-dihydrofuran Derivatives. Chem Eur J 2008, 14, 4263. <http://dx.doi.org/10.1002/chem.200800167>
  • Zheng Zilong, Ma Shengming, Jiang Xuefeng, Ma Xiaojing: Controllable Cyclization Reactions of 2-(2′,3′-Allenyl)acetylacetates Catalyzed by Gold and Palladium Affording Substituted Cyclopentene and 4,5-Dihydrofuran Derivatives with Distinct Selectivity. Chem Eur J 2008, 14, 8572. <http://dx.doi.org/10.1002/chem.200800793>
  • Jiang Huanfeng, Liu Xiaohang, Zhou Lei: First Synthesis of 1-Chlorovinyl Allenes via Palladium-Catalyzed Allenylation of Alkynoates with Propargyl Alcohols. Chem Eur J 2008, 14, 11305. <http://dx.doi.org/10.1002/chem.200801843>
  • Bai Tao, Xue Peng, Zhang Li, Ma Shengming, Jia Guochen: An efficient synthesis of 2-vinylic cyclic 1,3-alkadienes via the Cp*Ru(ii)-catalyzed intermolecular coupling reactions of alkynes and cyclic allenes. Chem Commun 2008, 2929. <http://dx.doi.org/10.1039/b801500g>
  • Bai Tao, Ma Shengming, Jia Guochen: Rh(I)-catalyzed three-component reaction of 2,3-allenoates, organoboronic acids, and aldehydes. An efficient synthesis of α,β-unsaturated δ-lactones. Tetrahedron 2007, 63, 6210. <http://dx.doi.org/10.1016/j.tet.2007.03.021>
  • Gu Zhenhua, Ma Shengming: Pd(OAc)2-Catalyzed Coupling/Cyclization of 2,3-Allenoic Acids and Methyl Propiolate: Observation of Double 1,7-Hydrogen Shifts. Angew Chem 2006, 118, 6148. <http://dx.doi.org/10.1002/ange.200601699>
  • Gu Zhenhua, Ma Shengming: Pd(OAc)2-Catalyzed Coupling/Cyclization of 2,3-Allenoic Acids and Methyl Propiolate: Observation of Double 1,7-Hydrogen Shifts. Angew Chem Int Ed 2006, 45, 6002. <http://dx.doi.org/10.1002/anie.200601699>
  • Ma Shengming, Gu Zhenhua, Deng Youqian: From allene to allene: a palladium-catalyzed approach to β-allenyl butenolides and their application to the synthesis of polysubstituted benzene derivatives. Chem Commun 2006, 94. <http://dx.doi.org/10.1039/b513371h>
  • Ma Shengming, Lu Ping, Lu Lianghua, Hou Hairong, Wei Jiemin, He Qiwen, Gu Zhenhua, Jiang Xuefeng, Jin Xing: What Can a Metal Catalyst Do with Allenes? One-Step Formation of Steroid Scaffolds from Readily Available Starting Materials. Angew Chem 2005, 117, 5409. <http://dx.doi.org/10.1002/ange.200501350>
  • Ma Shengming, Lu Ping, Lu Lianghua, Hou Hairong, Wei Jiemin, He Qiwen, Gu Zhenhua, Jiang Xuefeng, Jin Xing: What Can a Metal Catalyst Do with Allenes? One-Step Formation of Steroid Scaffolds from Readily Available Starting Materials. Angew Chem Int Ed 2005, 44, 5275. <http://dx.doi.org/10.1002/anie.200501350>
  • Chun-Ling Fu, Sheng-Ming Ma: NaSO2Ph Induced Exclusive Isomerization of 1,2-Allenyl Sulfoxides to 2-Alkynylic Phenyl Sulfoxides. Chin J Chem 2005, 23, 729. <http://dx.doi.org/10.1002/cjoc.200590729>
  • Helms Matthias, Schade Wolfgang, Pulz Robert, Watanabe Toshiko, Al-Harrasi Ahmed, Fišera Lubor, Hlobilová Iva, Zahn Gernot, Reißig Hans-Ulrich: Stereodivergent Syntheses of Highly Substituted Enantiopure 4-Alkoxy-3,6-dihydro-2H-1,2-oxazines by Addition of Lithiated Alkoxyallenes to Carbohydrate-Derived Aldonitrones. Eur J Org Chem 2005, 2005, 1003. <http://dx.doi.org/10.1002/ejoc.200400627>
  • Helms Matthias, Reißig Hans-Ulrich: Ozonolyses of Enantiopure 4-Alkoxy-3,6-dihydro-2H-1,2-oxazines:An Expedient Route to Functionalized α-Amino-β-hydroxy Esters. Eur J Org Chem 2005, 2005, 998. <http://dx.doi.org/10.1002/ejoc.200400734>
  • Kaden Silvia, Brockmann Mirjam, Reissig Hans-Ulrich: Syntheses of Enantiomerically Pure 2-Substituted Pyrrolidin-3-onesvia Lithiated Alkoxyallenes - An Auxiliary-Based Synthesis of both Enantiomers of the Antibiotic Anisomycin. HCA 2005, 88, 1826. <http://dx.doi.org/10.1002/hlca.200590143>
  • Fu Chunling, Ma Shengming: Highly Regio- and Stereoselective Synthesis of 2(E),4-Alkadienoates via the Pd(0)-Catalyzed Reaction of Aryl Halides with 3,4-Alkadienoates. Org Lett 2005, 7, 1707. <http://dx.doi.org/10.1021/ol0473389>
  • Pulz Robert, Al-Harrasi Ahmed, Reissig Hans-Ulrich: New Polyhydroxylated Pyrrolidines Derived from Enantiopure 3,6-Dihydro-2H-1,2-oxazines. Org Lett 2002, 4, 2353. <http://dx.doi.org/10.1021/ol0260573>