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Pure Appl. Chem., 1983, Vol. 55, No. 11, pp. 1807-1822

Some recent advances in the use of titanium reagents for organic synthesis

D. Seebach, A. K. Beck, M. Schiess, L. Widler and A. Wonnacott

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  • Petruzziello Diego, Stenta Marco, Mazzanti Andrea, Cozzi Pier Giorgio: A Rational Approach Towards a New Ferrocenyl Pyrrolidine for Stereoselective Enamine Catalysis. Chem. Eur. J. 2013, 19, 7696. <>
  • 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. <>
  • Fleury Lauren M., Kosal Andrew D., Masters James T., Ashfeld Brandon L.: Cooperative Titanocene and Phosphine Catalysis: Accelerated C–X Activation for the Generation of Reactive Organometallics. J. Org. Chem. 2013, 78, 253. <>
  • Braun Manfred: Die Diaryl(oxy)methyl-Gruppe: mehr als ein unbeteiligter Zuschauer in chiralen Auxiliaren, Katalysatoren und Dotierstoffen. angew chemie 2012, 124, 2600. <>
  • Braun Manfred: The Diaryl(oxy)methyl Group: More than an Innocent Bystander in Chiral Auxiliaries, Catalysts, and Dopants. Angew Chem Int E 2012, 51, 2550. <>
  • Pichota Arkadius, Gramlich Volker, Beck Albert K., Seebach Dieter: Preparation and Characterization of New C2- and C1-Symmetric Nitrogen, Oxygen, Phosphorous, and Sulfur Derivatives and Analogs of TADDOL. Part I. HCA 2012, 95, 1239. <>
  • Haleema Simimole, Sasi Paleapadam Vavan, Ibnusaud Ibrahim, Polavarapu Prasad L., Kagan Henri B.: Enantiomerically pure compounds related to chiral hydroxy acids derived from renewable resources. RSC Adv. 2012, 2, 9257. <>
  • Sandberg Thomas, Eklund Patrik, Hotokka Matti: Conformational Solvation Studies of LIGNOLs with Molecular Dynamics and Conductor-Like Screening Model. IJMS 2012, 13, 9845. <>
  • Seebach Dieter: Erzeugung sekundärer, tertiärer und quartärer Zentren durch geminale Disubstitution von Carbonyl-Sauerstoffatomen. Angew Chem 2011, 123, 99. <>
  • Seebach Dieter: Generation of Secondary, Tertiary, and Quaternary Centers by Geminal Disubstitution of Carbonyl Oxygens. Angew Chem Int Ed 2011, 50, 96. <>
  • Sandberg Thomas, Brusentsev Yury, Eklund Patrik, Hotokka Matti: Structural analysis of sterically hindered 1,4-diols from the naturally occurring lignan hydroxymatairesinol a quantum chemical study. Int Quant Chem 2011, 111, 4309. <>
  • Seebach Dieter, Grošelj Uroš, Badine D. Michael, Schweizer W. Bernd, Beck Albert K.: Isolation and X-Ray Structures of Reactive Intermediates of Organocatalysis with Diphenylprolinol Ethers and with Imidazolidinones. HCA 2008, 91, 1999. <>
  • Guillena Gabriela, Nájera Carmen, Ramón Diego J.: Enantioselective direct aldol reaction: the blossoming of modern organocatalysis. Tet Asymm 2007, 18, 2249. <>
  • Tietze Lutz F., Ott Christian, Frey Urban: Enantioselective Diels-Alder Reactions: NMR Spectroscopy of a Chiral Titanium Lewis Acid under High Pressure. Liebigs Ann /Recueil 2006, 1996, 63. <>
  • Braun Manfred, Hahn Antje, Engelmann Marco, Fleischer Ralf, Frank Walter, Kryschi Carola, Haremza Sylke, Kürschner Katrin, Parker Robert: Bis-Chelated Imine-Alkoxytitanium Complexes: Novel Chiral Dopants with High Helical Twisting Power in Liquid Crystals. Chem Eur J 2005, 11, 3405. <>
  • Adler Martin, Adler Sandra, Boche Gernot: Tetrahedral intermediates in reactions of carboxylic acid derivatives with nucleophiles. J Phys Org Chem 2005, 18, 193. <>
  • Jászay Zsuzsa M., Németh Gábor, Pham Truong Son, Petneházy Imre, Grün Alajos, Tőke László: Catalytic enantioselective Michael addition in the synthesis of α-aminophosphonates. Tet Asymm 2005, 16, 3837. <>
  • Seebach Dieter, Kimmerlin Thierry, Šebesta Radovan, Campo Marino A., Beck Albert K.: How we drifted into peptide chemistry and where we have arrived at. Tetrahedron 2004, 60, 7455. <>
  • Alexeev Yu.E., Vasilchenko I.S., Kharisov B.I., Blanco L.M., Garnovskii A.D., Zhdanov Yu.A.: Review: synthetically modified carbohydrates as ligands. J Coord Chem 2004, 57, 1447. <>
  • Heckel Alexander, Seebach Dieter: Preparation and Characterization of TADDOLs Immobilized on Hydrophobic Controlled-Pore-Glass Silica Gel and Their Use in Enantioselective Heterogeneous Catalysis. Chem Eur J 2002, 8, 559. <<559::AID-CHEM559>3.0.CO;2-1>
  • Seebach Dieter, Beck Albert K., Heckel Alexander: TADDOLe, ihre Derivate und Analoga – vielseitige chirale Hilfsstoffe. Angew Chem 2001, 113, 96. <<96::AID-ANGE96>3.0.CO;2-B>
  • Seebach Dieter, Beck Albert K., Heckel Alexander: TADDOLs, Their Derivatives, and TADDOL Analogues: Versatile Chiral Auxiliaries. Angewandte Chemie-Int Ed 2001, 40, 92. <<92::AID-ANIE92>3.0.CO;2-K>
  • Pastor Isidro M, Yus Miguel: Functionalised organotitanium compounds: from lithium to titanium intermediates in chemoselective reactions with carbonyl compounds. Tetrahedron 2001, 57, 2365. <>
  • Alexakis Alexandre, Burton Jonathan, Vastra Johann, Benhaim Cyril, Fournioux Xavier, van den Heuvel Alexandra, Levêque Jean-Marc, Mazé Frédérique, Rosset Stephane: Synthesis and Application of Chiral Phosphorus Ligands Derived from TADDOL for the Asymmetric Conjugate Addition of Diethyl Zinc to Enones. Eur J Org Chem 2000, 2000, 4011. <<4011::AID-EJOC4011>3.0.CO;2-D>
  • Fleischer Ralf, Wunderlich Hartmut, Braun Manfred: Synthesis and Structure Determination of Novel Chiral Imine-Alkoxytitanium Complexes. Eur J Org Chem 1998, 1998, 1063. <<1063::AID-EJOC1063>3.0.CO;2-W>
  • Beck Albert K., Dobler Max, Plattner Dietmar A.: TADDOLs Under Closer Scrutiny - why bulky substituents make it all different. HCA 1997, 80, 2073. <>
  • Kuball Hans-Georg, Weiß Bernhard, Beck Albert K., Seebach Dieter: TADDOLs with Unprecedented Helical Twisting Power in Liquid Crystals. Preliminary communication. HCA 1997, 80, 2507. <>
  • Ramón Diego J, Yus Miguel: Camphorsulfonamide derivatives: a new class of chiral catalysts for the titanium alkoxide-promoted addition of dialkylzinc to aldehydes. Tet Asymm 1997, 8, 2479. <>
  • Seebach Dieter, Marti Roger E., Hintermann Tobias: Polymer- and Dendrimer-Bound Ti-TADDOLates in Catalytic (and Stoichiometric) Enantioselective Reactions: Are pentacoordinate cationic Ti complexes the catalytically active species?. HCA 1996, 79, 1710. <>
  • Toda F., Tanaka K., Foces-Foces C., Infantes L., Claramunt R. M., López C., Elguero J.: Host-guest chemistry. The structure and proton disorder of the three-component crystal formed by 3(5)-methyl-4-nitropyrazole, (R, R)-(−)-trans-4,5-bis (hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolane and toluene. J Phys Org Chem 1996, 9, 611. <<611::AID-POC821>3.0.CO;2-M>
  • Quinkert Gerhard, Del Grosso Michael, Döring Astrid, Döring Wolfgang, Schenkel Ralf I., Bauch Markus, Dambacher Gernot T., Bats Jan W., Zimmermann Gottfried, Dürner Gerd: Total Synthesis with a Chirogenic Opening Move Demonstrated on Steroids with Estrane or 18a-Homoestrane Skeleton. HCA 1995, 78, 1345. <>
  • Schäfer Harald, Seebach Dieter: Enantioselective conjugate addition of primary dialkylzinc reagents to 2-aryl- and 2-heteroaryl-nitroolefins mediated by titanium-TADDOLates preparation of enantioenriched 2-aryl-alkylamines. Tetrahedron 1995, 51, 2305. <>
  • Mahrwald Rainer: Stereoselective aldol reaction using titanium ate complexes -an efficient method for achieving anti aldol selectivity. Tetrahedron 1995, 51, 9015. <>
  • Harada Kousuke, Urabe Hirokazu, Sato Fumie: Generation and reactions of low-valent titanium alkoxide-acetylene complexes. A practical preparation of allyl alcohols. Tetrahetron Lett 1995, 36, 3203. <>
  • Ito Yoshio N., Ariza Xavier, Beck Albert K., Boháč Andrej, Ganter Camille, Gawley Robert E., Kühnle Florian N. M., Tuleja Juraj, Wang Yan Ming, Seebach Dieter: Preparation and Structural Analysis of Several New α,α,α′,α′-Tetraaryl-1,3-dioxolane-4,5-dimethanols (TADDOL's) and TADDOL analogs, their evaluation as titanium ligands in the enantioselective addition of methyltitanium and diethylzinc reagents to benzaldehyde, and refinement of the mechanistic hypothesis. HCA 1994, 77, 2071. <>
  • Seebach Dieter, Beck Albert K., Schmidt Beat, Wang Yan Ming: Enantio- and diastereoselective titanium-TADDOLate catalyzed addition of diethyl and bis(3-buten-1-yl) zinc to aldehydes a full account with preparative details. Tetrahedron 1994, 50, 4363. <>
  • Seebach Dieter, Hayakawa Michiya, Sakaki Jun-ichi, Schweizer W.Bernd: Derivatives of α,α,α′,α′-Tetraaryl-2,2-dimethyl-1,3-dioxolan-4,5-dimethanol (TADDOL) containing nitrogen, sulfur, and phosphorus atoms. New ligands and auxiliaries for enantioselective reactions. Tetrahedron 1993, 49, 1711. <>
  • Quinkert Gerhard, Becker Heinrich, Del Grosso Michael, Dambacher Gernot, Bats Jan W., Dürner Gerd: Reduction of conformational space by 1,2-diketone·Lewis acid chelates. Tetrahetron Lett 1993, 34, 6885. <>
  • Kauffmann Thomas, Kieper Hansjörg: Alkyleisen- und Alkylcobalt-Reagenzien, V[1] Anticheleselektive Cyanoalkylierungen mit Cyanoalkyl-Derivaten von Eisen(II), Titan(IV) und weiteren Übergangsmetallen. Chem Ber 1992, 125, 907. <>
  • Seebach Dieter, Plattner Dietmar A., Beck Albert K., Wang Yan Ming, Hunziker Daniel, Petter Walter: On the Mechanisms of Enantioselective Reactions Using α,α,α′,α′ -Tetraaryl-1,3-dioxolane-4,5-dimethanol(TADDOL)-Derived Titanates: Differences betweenC2- andC1-symmetrical TADDOLs - facts, implications and generalizations. HCA 1992, 75, 2171. <>
  • Gundersen Lise-Lotte, Rise Frode, Undheim Kjell: Aryl- and alkynyltri-isopropoxytitanium reagents in regioselective carbon-carbon bond formation in azines. Tetrahedron 1992, 48, 5647. <>
  • von dem Bussche-Hünnefeld Joanna Linda, Seebach Dieter: Enantioselective preparation of sec. Alcohols from aldehydes and dialkyl zinc compounds, generated in situ from Grignard reagents, using substoichiometric amounts of TADDOL-titanates. Tetrahedron 1992, 48, 5719. <>
  • 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. <>
  • Schmidt Beat, Seebach Dieter: Katalytische und stöchiometrische enantioselektive Additionen von Diethylzink an Aldehyde mit Hilfe eines neuartigen chiralen Spirotitanats. Angew Chem 1991, 103, 100. <>
  • Seebach Dieter: Organische Synthese — wohin?. Angew Chem 1990, 102, 1363. <>
  • Adams Christopher M., Schemenaur John E.: Chemoselective Carbonyl Reduction Mediated By Low-Valent Titanium. Synth Common 1990, 20, 2359. <>
  • Stanchev Stephan, Hesse Manfred: An Unexpected Asymmetric Reduction of 4-(1-Nitro-2-oxocyclododecyl)butan-2-one. Determination of the absolute configuration of (-)-15-hexadecanolide. HCA 1989, 72, 1052. <>
  • Seebach Dieter: Struktur und Reaktivität von Lithiumenolaten, vom Pinakolon zur selektivenC-Alkylierung von Peptiden – Schwierigkeiten und Möglichkeiten durch komplexe Strukturen. Angew Chem 1988, 100, 1685. <>
  • Seebach Dieter: Structure and Reactivity of Lithium Enolates. From Pinacolone to SelectiveC-Alkylations of Peptides. Difficulties and Opportunities Afforded by Complex Structures. Angew Chem Int Ed Engl 1988, 27, 1624. <>
  • Seebach Dieter, Beck Albert K., Imwinkelzied René, Roggo Silvio, Wonnacott Anne: Chirale Alkoxytitan(IV)-Komplexe für enantioselektive nucleophile Additionen an Aldehyde und alsLewis-Säuren inDiels-Alder-Reaktionen. HCA 1987, 70, 954. <>
  • Betschart Claudia, Seebach Dieter: Aminierende reduktive Kupplung aromatischer Aldehyde mit niervalenten Titan-Reagenzien zu 1,2-Diarylethylendiaminen. HCA 1987, 70, 2215. <>
  • Hegedus Louis S.: Transition metals in organic synthesis annual survey covering the year 1984. J Organomet Chem 1986, 298, 207. <>
  • Siglmüller Franz, Herrmann Rudolf, Ugi Ivar: Chiral perrocenylalkylamines from (-)-menthone. Tetrahedron 1986, 42, 5931. <>
  • Siegel Craig, Thornton Edward R.: Very high diastereofacial selectivities in convenient titanium—mediated aldol reactions. Tetrahetron Lett 1986, 27, 457. <>
  • Imwinkelried René, Seebach Dieter: Allylierung von Aldehyden unter Veretherung mit Dialkoxydichlorotitan und Allyltrimethylsilan; eine asymmetrische Variante der Sakurai-Reaktion. Angew Chem 1985, 97, 781. <>
  • Imwinkelried René, Seebach Dieter: Allylation of Aldehydes with Etherification by Dialkoxydichlorotitanium/Allyltrimethylsilane; an Asymmetric Variant of the Sakurai Reaction. Angew Chem Int Ed Engl 1985, 24, 765. <>
  • Widler Leo, Weber Theoder, Seebach Dieter: d1- und d3-selektive Umsetzungen von schwefelsubstituierten Allyl-Titan-Derivaten mit Aldehyden und Ketonen. Chem Ber 1985, 118, 1329. <>
  • Seebach Dieter, Beck Albert K., Roggo Silvio, Wonnacott Anne: Enantioselektive Addition von Arylgruppen an aromatische Aldehyde mit Aryltitan-Binaphthol-Derivaten. Chem Ber 1985, 118, 3673. <>
  • Rise Frode, Undheim Kjell: Regioselectivity in reactions of alkynylmetal complexes with pyrimidinones. J Organomet Chem 1985, 291, 139. <>
  • Nájera Carmen, Yus Miguel, Seebach Dieter: C-Metallierte chirale Aloxide als d2- und d3-Reagenzien für die Synthese enantiomerenreiner Produkte (EPC-Synthese). HCA 1984, 67, 289. <>
  • Aono Tetsuya, Hesse Manfred: Synthesis of 14-Membered Lactones from Cyclooctanone. HCA 1984, 67, 1448. <>
  • Imwinkelried René, Seebach Dieter: Aminierende, reduktive Kupplung aromatischer Aldehyde mit Tris(dialkylamino)methylvanandium (IV) zuN,N,N′,N′-Tetraaalkyl-1,2-diaryläthylendiaminen. HCA 1984, 67, 1496. <>
  • Seebach Dieter, Betschart Clauida, Schiess Martin: Diastereoselektive synthese neuartigerMannich-Basen mittels titanderivaten, vorläufige mitteilung. HCA 1984, 67, 1593. <>
  • Seebach Dieter, Naef Reto, Calderari Giorgio: (α-Alkylation of α-heterosubstituted carboxylic acids without racemization. Tetrahedron 1984, 40, 1313. <>