Pure Appl. Chem., 1990, Vol. 62, No. 10, pp. 1933-1940
http://dx.doi.org/10.1351/pac199062101933
Synthetic applications of metallate rearrangements
CrossRef Cited-by Linking
- Khairallah George N., Saleeba Kirsty A., Chow Sharon, Eger Wilhelm, Williams Craig M., O’Hair Richard A.J.: CH and CC bond activation reactions in silver alkynyl cluster cations, RCCAg2+. International Journal of Mass Spectrometry 2013, 354-355, 229. <http://dx.doi.org/10.1016/j.ijms.2013.07.010>
- 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>
- Meiries Sébastien, Bartoli Alexandra, Decostanzi Mélanie, Parrain Jean-Luc, Commeiras Laurent: Directed studies towards the total synthesis of (+)-13-deoxytedanolide: simple and convenient synthesis of the C8–C16 fragment. Org. Biomol. Chem. 2013, 11, 4882. <http://dx.doi.org/10.1039/c3ob40674a>
- Stec Jozef, Henderson Alan R., Whitby Richard J.: Synthesis of homopropargyl alcohols via insertion of allenyl carbenoids into acyclic organozirconium bonds. Tetrahedron Letters 2012, 53, 1112. <http://dx.doi.org/10.1016/j.tetlet.2011.12.081>
- Lefranc Julien, Fournier Anne M., Mingat Gaëlle, Herbert Simon, Marcelli Tommaso, Clayden Jonathan: Intramolecular Vinylation of Secondary and Tertiary Organolithiums. S J Am Chem Soc 2012, 134, 7286. <http://dx.doi.org/10.1021/ja301591m>
- Leverett Carolyn A., Purohit Vikram C., Johnson Alex G., Davis Rebecca L., Tantillo Dean J., Romo Daniel: Dyotropic Rearrangements of Fused Tricyclic β-Lactones: Application to the Synthesis of (−)-Curcumanolide A and (−)-Curcumalactone. J. Am. Chem. Soc. 2012, 134, 13348. <http://dx.doi.org/10.1021/ja303414a>
- M. Hodgson David, A. H. Stent Matthew, S. Paton Robert, X. Wilson Francis: Unusual Base-Induced Rearrangement of exo-9-Oxabicyclo[4.2.1]non-7-ene Oxide to exo-8-Hydroxybicyclo[3.3.0]octan-2-one. Heterocycle 2012, 84, 625. <http://dx.doi.org/10.3987/COM-11-S(P)35>
- Stec Jozef, Thomas Emma, Dixon Sally, Whitby Richard J.: Tandem Insertion of Halocarbenoids and Lithium Acetylides into Zirconacycles: A Novel Rearrangement to Zirconium Alkenylidenates by β-Addition to an Alkynyl Zirconocene. Chemistry A European Journal 2011, 17, 4896. <http://dx.doi.org/10.1002/chem.201002962>
- de Lemos Elsa, Agouridas Evangelos, Sorin Geoffroy, Guerreiro Antonio, Commerçon Alain, Pancrazi Ange, Betzer Jean-François, Lannou Marie-Isabelle, Ardisson Janick: Conception, Synthesis, and Biological Evaluation of Original Discodermolide Analogues. Chemistry A European Journal 2011, 17, 10123. <http://dx.doi.org/10.1002/chem.201100675>
- Nguyen Tan Tai, Marquise Nada, Chevallier Floris, Mongin Florence: Deprotonative Metalation of Aromatic Compounds by Using an Amino-Based Lithium Cuprate. Chemistry A European Journal 2011, 17, 10405. <http://dx.doi.org/10.1002/chem.201100990>
- Davis Rebecca L., Leverett Carolyn A., Romo Daniel, Tantillo Dean J.: Switching between Concerted and Stepwise Mechanisms for Dyotropic Rearrangements of β-Lactones Leading to Spirocyclic, Bridged γ-Butyrolactones. J Org Chern 2011, 76, 7167. <http://dx.doi.org/10.1021/jo2012175>
- Rijs Nicole J., Yates Brian F., O'Hair Richard A. J.: Dimethylcuprate Undergoes a Dyotropic Rearrangement. Chem Eur J 2010, 16, 2674. <http://dx.doi.org/10.1002/chem.200903510>
- KOCIENSKI P., BARBER C.: ChemInform Abstract: Synthetic Applications of Metallate Rearrangements. ChemInform 2010, 22, no. <http://dx.doi.org/10.1002/chin.199107317>
- Black Fiona J., Kocienski Philip J.: Synthesis of phalluside-1 and Sch II using 1,2-metallate rearrangements. Org Biomol Chem 2010, 8, 1188. <http://dx.doi.org/10.1039/b920285d>
- Kerrigan Michael H., Jeon Sang-Jin, Chen Young K., Salvi Luca, Carroll Patrick J., Walsh Patrick J.: One-Pot Multicomponent Coupling Methods for the Synthesis of Diastereo- and Enantioenriched (Z)-Trisubstituted Allylic Alcohols. J Am Chem Soc 2009, 131, 8434. <http://dx.doi.org/10.1021/ja809821x>
- Gais Hans‐Joachim, Rao C. Venkateshwar, Loo Ralf: Anionic Cross‐Coupling Reaction of α‐Metallated Alkenyl Sulfoximines and Alkenyl Sulfoximines with Cuprates Featuring a 1,2‐Metal‐Ate Rearrangement of Sulfoximine‐Substituted Higher Order Alkenyl Cuprates and an α‐Metallation of Alkenyl Sulfoximines by Cuprates. Chem Eur J 2008, 14, 6510. <http://dx.doi.org/10.1002/chem.200800455>
- de Lemos Elsa, Porée François-Hugues, Bourin Arnaud, Barbion Julien, Agouridas Evangelos, Lannou Marie-Isabelle, Commerçon Alain, Betzer Jean-François, Pancrazi Ange, Ardisson Janick: Total Synthesis of Discodermolide: Optimization of the Effective Synthetic Route. Chem Eur J 2008, 14, 11092. <http://dx.doi.org/10.1002/chem.200801478>
- Abramovitch Adi, Marek Ilan: Zinc Homologation-Elimination Reaction of α-Sulfinyl Carbanions as a New Route to Olefins. Eur J Org Chem 2008, 2008, 4924. <http://dx.doi.org/10.1002/ejoc.200800529>
- Florence Gordon J., Gardner Nicola M., Paterson Ian: Development of practical syntheses of the marine anticancer agents discodermolide and dictyostatin. Nat Prod Rep 2008, 25, 342. <http://dx.doi.org/10.1039/b705661n>
- Howells Dean, Robiette Raphaël, Fang Guang Y., Knowles Luke S., Woodrow Michael D., Harvey Jeremy N., Aggarwal Varinder K.: Reactions of silyl-stabilised sulfur ylides with organoboranes: enantioselectivity, mechanism, and understanding. Org Biomol Chem 2008, 6, 1185. <http://dx.doi.org/10.1039/b718496d>
- SHIMIZU Masaki, HIYAMA Tamejiro: Polyborylated reagents for modern organic synthesis. Proc Jpn Acad Ser B 2008, 84, 75. <http://dx.doi.org/10.2183/pjab.84.75>
- Fang Guang Yu, Aggarwal Varinder K.: Asymmetric Synthesis of α-Substituted Allyl Boranes and Their Application in the Synthesis of Iso-agatharesinol. Angew Chem 2007, 119, 363. <http://dx.doi.org/10.1002/ange.200603659>
- de Lemos Elsa, Porée François-Hugues, Commerçon Alain, Betzer Jean-François, Pancrazi Ange, Ardisson Janick: α-Oxygenated Crotyltitanium and Dyotropic Rearrangement in the Total Synthesis of Discodermolide. Angew Chem 2007, 119, 1949. <http://dx.doi.org/10.1002/ange.200604629>
- Fang Guang Yu, Aggarwal Varinder K.: Asymmetric Synthesis of α-Substituted Allyl Boranes and Their Application in the Synthesis of Iso-agatharesinol. Angew Chem Int Ed 2007, 46, 359. <http://dx.doi.org/10.1002/anie.200603659>
- de Lemos Elsa, Porée François-Hugues, Commerçon Alain, Betzer Jean-François, Pancrazi Ange, Ardisson Janick: α-Oxygenated Crotyltitanium and Dyotropic Rearrangement in the Total Synthesis of Discodermolide. Angew Chem Int Ed 2007, 46, 1917. <http://dx.doi.org/10.1002/anie.200604629>
- Thomas Emma, Dixon Sally, Whitby Richard J.: The regiochemistry of zirconacycle elaboration. Tetrahedron 2007, 63, 11686. <http://dx.doi.org/10.1016/j.tet.2007.08.105>
- Schuppan Julia, Wehlan Hermut, Keiper Sonja, Koert Ulrich: Apoptolidinone A: Synthesis of the Apoptolidin A Aglycone. Chem Eur J 2006, 12, 7364. <http://dx.doi.org/10.1002/chem.200600461>
- Thomas Emma, Kasatkin Alexander N., Whitby Richard J.: Cyclopropyl carbenoid insertion into alkenylzirconocenes—a convergent synthesis of alkenylcyclopropanes and alkylidenecyclopropanes. Tetrahetron Lett 2006, 47, 9181. <http://dx.doi.org/10.1016/j.tetlet.2006.10.132>
- Montserrat Martínez M., Hoppe Dieter: Novel Approach to the (-)-Sparteine-Mediated Synthesis of Kainoids:Total Synthesis of (-)-α-Kainic Acid by (-)-Sparteine-Mediated Deprotonation. Eur J Org Chem 2005, 2005, 1427. <http://dx.doi.org/10.1002/ejoc.200400824>
- Kondo Junichi, Inoue Atsushi, Ito Yuki, Shinokubo Hiroshi, Oshima Koichiro: Preparation of α-silyl- or α,α-bis(silyl)-substituted alkylcopper reagents and their synthetic use. Tetrahedron 2005, 61, 3361. <http://dx.doi.org/10.1016/j.tet.2005.01.101>
- Wipf Peter, Nunes Ruth L.: Selective carbon–carbon bond formations with alkenylzirconocenes. Tetrahedron 2004, 60, 1269. <http://dx.doi.org/10.1016/j.tet.2003.12.018>
- Hodgson David M., Maxwell Christopher R., Miles Timothy J., Paruch Edyta, Matthews Ian R., Witherington Jason: Organolithium-induced enantioselective alkylative double ring-opening of epoxides: synthesis of enantioenriched unsaturated amino alcohols. Tetrahedron 2004, 60, 3611. <http://dx.doi.org/10.1016/j.tet.2004.02.055>
- Kasatkin Aleksandra, Whitby Richard J.: A convergent regiospecific synthesis of zirconium enolates. Tetrahedron 2003, 59, 9857. <http://dx.doi.org/10.1016/j.tet.2003.09.022>
- Hodgson David M, Miles Timothy J, Witherington Jason: Organolithium-induced synthesis of acyclic unsaturated amino alcohols from epoxides of dihydropyrroles and tetrahydropyridines. Tetrahedron 2003, 59, 9729. <http://dx.doi.org/10.1016/j.tet.2003.10.010>
- Marr Felix, Fröhlich Roland, Wibbeling Birgit, Diedrich Christian, Hoppe Dieter: The Synthesis and Configurational Stability of Enantioenriched α-Thioallyllithium Compounds and the Stereochemical Course of Their Electrophilic Substitution. Eur J Org Chem 2002, 2002, 2970. <http://dx.doi.org/10.1002/1099-0690(200209)2002:17<2970::AID-EJOC2970>3.0.CO;2-J>
- Inoue Atsushi, Kondo Junichi, Shinokubo Hiroshi, Oshima Koichiro: Reactions ofgem-Dibromo Compounds with Trialkylmagnesate Reagents to Yield Alkylated Organomagnesium Compounds. Chem Eur J 2002, 8, 1730. <http://dx.doi.org/10.1002/1521-3765(20020402)8:7<1730::AID-CHEM1730>3.0.CO;2-6>
- Kurahashi Takuya, Hata Takeshi, Masai Hirokazu, Kitagawa Hirotaka, Shimizu Masaki, Hiyama Tamejiro: Geminal dimetalation of alkylidene-type carbenoids with silylboranes and diborons. Tetrahedron 2002, 58, 6381. <http://dx.doi.org/10.1016/S0040-4020(02)00648-8>
- Kondo Junichi, Inoue Atsushi, Shinokubo Hiroshi, Oshima Koichiro: Generation and regioselective reactions of α,α-bis(silyl)-substituted allylcopper reagents—synthesis of 1,1-disilylalkenes. Tetrahetron Lett 2002, 43, 2399. <http://dx.doi.org/10.1016/S0040-4039(02)00259-9>
- Kondo Junichi, Inoue Atsushi, Shinokubo Hiroshi, Oshima Koichiro: Synthese von (α-Silylalkyl)magnesium- verbindungen aus R3SiCHBr2 und einem Trialkylmagnesat. Angew Chem 2001, 113, 2146. <http://dx.doi.org/10.1002/1521-3757(20010601)113:11<2146::AID-ANGE2146>3.0.CO;2-S>
- Kondo Junichi, Inoue Atsushi, Shinokubo Hiroshi, Oshima Koichiro: Alkylative Preparation ofα-Silylalkylmagnesium from R3SiCHBr2 Using a Magnesate Reagent. Angew Chem Int Ed 2001, 40, 2085. <http://dx.doi.org/10.1002/1521-3773(20010601)40:11<2085::AID-ANIE2085>3.0.CO;2-K>
- Betzer Jean-Fran��ois, Ardisson Janick, Pancrazi Ange: IMDA reaction in a synthetic approach towards a natural kijamicin aglycon analog. Comptes Rendus de l'Acad��mie des Sciences - Series IIC - Chemistry 2001, 4, 695. <http://dx.doi.org/10.1016/S1387-1609(01)01260-9>
- Deiters Alexander, Hoppe Dieter: Chiral induzierte, mit einer Eliminierung gekoppelte Lithium-En-Reaktion – Synthese von (+)-(3R,4R)-1,2-Dihydromultifiden. Angew Chem 1999, 111, 529. <http://dx.doi.org/10.1002/(SICI)1521-3757(19990215)111:4<529::AID-ANGE529>3.0.CO;2-2>
- Yamanoi Shigeo, Matsumoto Takashi, Suzuki Keisuke: Reaction of 1-iodoalkynes with allylzirconiums: Generation of alkylidene carbenoid via allylzirconation. Tetrahetron Lett 1999, 40, 2793. <http://dx.doi.org/10.1016/S0040-4039(99)00296-8>
- Madec David, Henryon Vivien, Férézou Jean-Pierre: Easy transformations of vinyl N,N-diisopropyl carbamates into silyl enol ethers or aldehydes by addition of methyllithium. Tetrahetron Lett 1999, 40, 8103. <http://dx.doi.org/10.1016/S0040-4039(99)01699-8>
- Kasatkin Alexander N, Whitby Richard J: Insertions of silylated carbenoids into vinylzirconocene chlorides. A convergent route to silyl-substituted allylzirconium reagents. Tetrahetron Lett 1999, 40, 9353. <http://dx.doi.org/10.1016/S0040-4039(99)01982-6>
- Braun Manfred: 1-Alkenyllithium-Reagentien mit einem Heteroatomsubstituenten in derα-Position: Carbanionen und Carbenoide zur C-C-Verknüpfung. Angew Chem 1998, 110, 444. <http://dx.doi.org/10.1002/(SICI)1521-3757(19980216)110:4<444::AID-ANGE444>3.0.CO;2-J>
- Wang Yigui, Sun Changjun, Deng Conghao: Ab initio studies on reaction H2C=C(OH)Li+CH3 + (CH3 -). SCI CHINA SER B 1998, 41, 587. <http://dx.doi.org/10.1007/BF02883020>
- Wang Yi-gui, Sun Chang-jun, Deng Cong-hao: A theoretical study of C2H3OLi. Journal of Molecular Structure: THEOCHEM 1998, 429, 207. <http://dx.doi.org/10.1016/S0166-1280(97)00354-0>
- Hoppe Dieter, Hense Thomas: Enantioselektive Synthese mit Lithium/(−)-Spartein-Carbanion-Paaren. Angew Chem 1997, 109, 2376. <http://dx.doi.org/10.1002/ange.19971092105>
- McDonald Frank E., Schultz Colleen C.: Sequential application of stereoselective syn-oxidation methodologies to natural product synthesis: A potentially biomimetic approach to the C12–C21 bistetrahydrofuran region of monensin. Tetrahedron 1997, 53, 16435. <http://dx.doi.org/10.1016/S0040-4020(97)01026-0>
- Kasatkin Aleksandr, Whitby Richard J: Zirconium mediated synthesis. Convergent access to terminal trienes, dienes, and dienynes. Tetrahetron Lett 1997, 38, 4857. <http://dx.doi.org/10.1016/S0040-4039(97)01012-5>
- Fargeas Valérie, Le Ménez Patrick, Berque Isabelle, Ardisson Janick, Pancrazi Ange: Studies in cuprate rearrangement and stannylcupration: Application to the stereo- and enantiospecific synthesis of a stannyldiene C10–C15 fragment of des-epoxy-rosaramycin. Tetrahedron 1996, 52, 6613. <http://dx.doi.org/10.1016/0040-4020(96)00315-8>
- Le Ménez Patrick, Fargeas Valérie, Poisson Jacques, Ardisson Jannick, Lallemand Jean-Yves, Pancrazi Ange: 1,2-metallate rearrangements: stannyl and (stannyl)vinyl transfers. Tetrahetron Lett 1994, 35, 7767. <http://dx.doi.org/10.1016/0040-4039(94)80113-4>
- Creton Isabelle, Marek Ilane, Brasseur Denis, Jestin Jean-Luc, Normant Jean-F.: Phenylthioacetylene as a source of stereodefined trisubstituted alkenes. Tetrahetron Lett 1994, 35, 6873. <http://dx.doi.org/10.1016/0040-4039(94)85028-3>
- Luker Tim, Whitby Richard J.: Elaboration of zirconacyclopentanes by sequential insertion of lithium chloroallylide and ketones or aldehydes. Tetrahetron Lett 1994, 35, 785. <http://dx.doi.org/10.1016/S0040-4039(00)75817-5>
- Boche Gernot, Bosold Ferdinand, Lohrenz John C. W., Opel Achim, Zulauf Peter: α-Oxygen-Substituted Organolithium Compounds and their Carbenoid Nature: Reactions with RLi and Other Nucleophiles, Experimental and IGLO-Calculated13C-NMR Shifts of the Carbenoid C Atom. Chem Ber 1993, 126, 1873. <http://dx.doi.org/10.1002/cber.19931260819>
- 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>
- Boche Gernot, Opel Achim, Marsch Michael, Harms Klaus, Hallera Friederike, Lohrenz John C. W., Thümmler Christina, Koch Wolfram: α-Oxygen-Substituted Organolithium Compounds and Their Carbenoid Nature: Calculations of the Configurational Stability and of LiCH2OH Model Structures, Crystal Structure of Diphenyl(trimethylsilyloxy)methyllithium · 3 THF, and the Stereochemistry of the (Reverse) Brook Rearrangement. Chem Ber 1992, 125, 2265. <http://dx.doi.org/10.1002/cber.19921251015>
- Hegedus Louis S.: Transition metals in organic synthesis annual survey covering the year 1990. J Organomet Chem 1992, 422, 301. <http://dx.doi.org/10.1016/0022-328X(92)88031-D>
- Nguyen Thinh, Negishi Ei-ichi: Carbon-carbon bond formation by the reaction of organolithiums with α-lithiated cyclic enol ethers. Stereoselective synthesis of β- and γ-hydroxy di- and tri-substituted alkenes. Tetrahetron Lett 1991, 32, 5903. <http://dx.doi.org/10.1016/S0040-4039(00)79422-6>