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Pure Appl. Chem., 1990, Vol. 62, No. 10, pp. 1999-2006

http://dx.doi.org/10.1351/pac199062101999

Metallated 2-alkenyl carbamates: chiral homoenolate reagents for asymmetric synthesis

D. Hoppe, Thomas Kramer, J.-R. Schwark and Oliver Zschage

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  • Mongin Florence, Harrison-Marchand Anne: Mixed AggregAte (MAA): A Single Concept for All Dipolar Organometallic Aggregates. 2. Syntheses and Reactivities of Homo/HeteroMAAs. Chem. Rev. 2013, 113, 7563. <http://dx.doi.org/10.1021/cr3002966>
  • Rosa David, Orellana Arturo: Palladium-catalyzed cross-coupling of cyclopropanol-derived ketone homoenolates with aryl bromides. Chem. Commun. 2013, 49, 5420. <http://dx.doi.org/10.1039/c3cc42080a>
  • Fournier Anne M., Nichols Christopher J., Vincent Mark A., Hillier Ian H., Clayden Jonathan: Lithium Choreography: Intramolecular Arylations of Carbamate-Stabilised Carbanions and Their Mechanisms Probed by In Situ IR Spectroscopy and DFT Calculations. Chem. Eur. J. 2012, 18, 16478. <http://dx.doi.org/10.1002/chem.201201761>
  • Ma Lu, Zhao Dongmei, Chen Lin, Wang Xin, Chen Yue-Lei, Shen Jingkang: (N,N-Diisopropylcarbamoyloxy)-methyl p-tolyl sulfone: preparation and application for the syntheses of 1,2-diols. Tetrahedron 2012, 68, 8704. <http://dx.doi.org/10.1016/j.tet.2012.08.025>
  • Pulis Alexander P., Aggarwal Varinder K.: Synthesis of Enantioenriched Tertiary Boronic Esters from Secondary Allylic Carbamates. Application to the Synthesis of C30 Botryococcene. S J Am Chem Soc 2012, 134, 7570. <http://dx.doi.org/10.1021/ja303022d>
  • HOPPE D., KRAEMER T., SCHWARK J.-R., ZSCHAGE O.: ChemInform Abstract: Metallated 2-Alkenyl Carbamates: Chiral Homoenolate Reagents for Asymmetric Synthesis. ChemInform 2010, 22, no. <http://dx.doi.org/10.1002/chin.199107312>
  • Enantioselektive Deprotonierungen und Protonierungen. Nachr Chem Tech Lab 2010, 39, 413. <http://dx.doi.org/10.1002/nadc.19910390408>
  • Chan Audrey, Scheidt Karl A.: Conversion of α,β-Unsaturated Aldehydes into Saturated Esters: An Umpolung Reaction Catalyzed by Nucleophilic Carbenes. Org Lett 2005, 7, 905. <http://dx.doi.org/10.1021/ol050100f>
  • Özlügedik Mustafa, Kristensen Jesper, Wibbeling Birgit, Fröhlich Roland, Hoppe Dieter: Nonracemic, Chiral Homoenolate Reagents Derived from (Cycloalk-1-enyl)methyl Carbamates and Evaluation of Their Configurational Stabilities. Eur J Org Chem 2002, 2002, 414. <http://dx.doi.org/10.1002/1099-0690(20022)2002:3<414::AID-EJOC414>3.0.CO;2-2>
  • Schlapbach Achim, Hoffmann Reinhard W.: (E)-α-Sulfonamidocrotylboronates as Reagents for the Stereoselective Homoaldol Synthesis. Eur J Org Chem 2001, 2001, 323. <http://dx.doi.org/10.1002/1099-0690(200101)2001:2<323::AID-EJOC323>3.0.CO;2-A>
  • Ahlbrecht Hubertus, Schmidt Rainer, Beyer Uwe: Asymmetric Synthesis of β-Methylated Aliphatic Ketones via Lithiated 3-[(S)-2-(Methoxymethyl)pyrrolidino]hex-3-ene⋆. Eur J Org Chem 1998, 1998, 1371. <http://dx.doi.org/10.1002/(SICI)1099-0690(199807)1998:7<1371::AID-EJOC1371>3.0.CO;2-K>
  • Hoppe Dieter, Hense Thomas: Enantioselektive Synthese mit Lithium/(−)-Spartein-Carbanion-Paaren. Angew Chem 1997, 109, 2376. <http://dx.doi.org/10.1002/ange.19971092105>
  • Schwarz Jacob B., Devine Paul N., Meyers A.I.: Chiral bicyclic Lactams as homoenolate equivalents: An asymmetric route to 5-substituted cyclohexenones. Tetrahedron 1997, 53, 8795. <http://dx.doi.org/10.1016/S0040-4020(97)90391-4>
  • Frances van Staden L., Bartels-Rahm Birgit, Emslie Neville D.: The Peterson olefination of benzyl carbamates. Tetrahetron Lett 1997, 38, 1851. <http://dx.doi.org/10.1016/S0040-4039(97)00222-0>
  • Ahlbrecht Hubertus, Kramer Andreas: Chiral Homoenolate Equivalents, V. Hydroxylakylation of Lithiated 3-[(S)-2-(Methoxymethyl)pyrrolidino]-1,3-diphenylpropene – An Asymmetric Homoaldol Reaction. Chem Ber 1996, 129, 1161. <http://dx.doi.org/10.1002/cber.19961291004>
  • Kaiser Bernd, Hoppe Dieter: Bildung und Nachweis enantiomeren-angereicherter und konfigurationsstabiler α-Thioalkyllithium-Verbindungen. Angew Chem 1995, 107, 344. <http://dx.doi.org/10.1002/ange.19951070313>
  • Hoppe Inga, Hoppe Dieter, Boche Gernot, Marsch Michael, Harms Klaus: Bildung von enantiomerenangereicherten Lithiumindeniden mit (−)-Spartein — Strukturen, stereospezifische Substitution, Einfluß des Lösungsmittels. Angew Chem 1995, 107, 2328. <http://dx.doi.org/10.1002/ange.19951071926>
  • Tochtermann Werner, Weidner Fritjof: Tetrahydrofurane und γ-Lactone, VII. Synthese und Reaktionen von γ,γ-disubstituierten γ-Lactonen – ein Weg zu funktionalisierten Dodecandisäure-Derivaten. Liebigs Ann Chem 1994, 1994, 593. <http://dx.doi.org/10.1002/jlac.199419940609>
  • Carstens Axel, Hoppe Dieter: Generation of a configurationally stable, enantioenriched α-oxy-α-methylbenzyllithium: Stereodivergence of its electrophilic substitution. Tetrahedron 1994, 50, 6097. <http://dx.doi.org/10.1016/S0040-4020(01)90461-2>
  • Ager David J., East Michael B.: The synthesis of carbohydrate derivatives from acyclic precursors. Tetrahedron 1993, 49, 5683. <http://dx.doi.org/10.1016/S0040-4020(01)87942-4>
  • Peschke Bernd, Lüßmann Jörg, Hoppe Dieter, Dyrbusch Zzmichael: Diastereo- and enantioselective synthesis of 1,2:5,6-diepoxy-4-hydroxyalkyl carbamates. – regioselective ring opening and their transformation into doublyC-branched deoxy sugar analogues. Chem Ber 1992, 125, 1421. <http://dx.doi.org/10.1002/cber.19921250620>
  • Zschage Oliver, Hoppe Dieter: Sparteine complexes of lithiated primary O-2-alkenyl carbamates stereochemistry of the lithium-titanium exchange and application for the synthesis of enantiomerically enriched γ-lactones. Tetrahedron 1992, 48, 5657. <http://dx.doi.org/10.1016/0040-4020(92)80016-9>
  • Zschage Oliver, Schwark Jan-Robert, Krämer Thomas, Hoppe Dieter: Enantiomerically enriched 1-(N,N-diisopropylcarbamoyloxy)-1,3-dimethylallyllithium: stereochemistry of the stannylation, titanation, and the homoaldol reaction. Tetrahedron 1992, 48, 8377. <http://dx.doi.org/10.1016/S0040-4020(01)86586-8>
  • Hafner Andreas, Duthaler Rudolf O., Marti Roger, Rihs Grety, Rothe-Streit Petra, Schwarzenbach Franz: Enantioselective syntheses with titanium carbohydrate complexes. Part 7. Enantioselective allyltitanation of aldehydes with cyclopentadienyldialkoxyallyltitanium complexes. S J Am Chem Soc 1992, 114, 2321. <http://dx.doi.org/10.1021/ja00033a005>
  • Marsch Michael, Harms Klaus, Zschage Oliver, Hoppe Dieter, Boche Gernot: η1-(1S,2E)-1-(N, N-Diisopropylcarbamoyloxy)-3-trimethylsilyl-allyllithium-(-)-Spartein: Struktur einer chiralen, Carbamoyloxy-substituierten Allyllithium-Verbindung. Angew Chem 1991, 103, 338. <http://dx.doi.org/10.1002/ange.19911030327>
  • Hanko Rudolf, Rabe Klaus, Dally Robert, Hoppe Dieter: Stereoselektive Synthese von cyclischen Hydroxyalkyl-Dipeptidisosteren über metallierteN,N-Dialkylcarbamidsäure-2-alkenylester. Angew Chem 1991, 103, 1725. <http://dx.doi.org/10.1002/ange.19911031242>