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Pure Appl. Chem., 1999, Vol. 71, No. 6, pp. 1053-1057

http://dx.doi.org/10.1351/pac199971061053

New Mitsunobu reagents in the C–C bond formation. Application to natural product synthesis

S. Itô and T. Tsunoda

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  • Noisier Anaïs F. M., Harris Craig S., Brimble Margaret A.: Novel preparation of chiral α-amino acids using the Mitsunobu–Tsunoda reaction. Chem. Commun. 2013, 49, 7744. <http://dx.doi.org/10.1039/c3cc44717k>
  • Yang Jianhai, Dai Liyan, Wang Xiaozhong, Chen Yingqi: Di-p-nitrobenzyl azodicarboxylate (DNAD): an alternative azo-reagent for the Mitsunobu reaction. Tetrahedron 2011, 67, 1456. <http://dx.doi.org/10.1016/j.tet.2010.12.036>
  • Imagawa Yosuke, Yoshikawa Syuhei, Fukuhara Tadahito, Hara Shoji: Conversion of MT-sulfone to a trifluoromethyl group by IF5: the application of an MT-sulfone anion as a trifluoromethyl anion equivalent. Chemical Communication 2011, 47, 9191. <http://dx.doi.org/10.1039/c1cc13232f>
  • Alajarín Mateo, Orenes Raúl-Angel, Berná José: Azodicarboxamides as Template Binding Motifs for the Building of Hydrogen-Bonded Molecular Shuttles. J Am Chem Soc 2010, 132, 10741. <http://dx.doi.org/10.1021/ja101151t>
  • Golantsov N. E., Karchava A. V., Yurovskaya M. A.: The Mitsunobu reaction in the chemistry of nitrogen-containing heterocyclic compounds. The formation of heterocyclic systems (review). Chem Heterocycl Compd 2008, 44, 263. <http://dx.doi.org/10.1007/s10593-008-0042-4>
  • KAKU Hiroto: Thermodynamically Controlled Deracemization Utilizing Inclusion Complexation. YAKUGAKU ZASSHI 2008, 128, 1431. <http://dx.doi.org/10.1248/yakushi.128.1431>
  • Prakash G. K. Surya, Chacko Sujith, Alconcel Steevens, Stewart Timothy, Mathew Thomas, Olah George A.: Stereoselective Monofluoromethylation of Primary and Secondary Alcohols by Using a Fluorocarbon Nucleophile in a Mitsunobu Reaction. Angew Chem 2007, 119, 5021. <http://dx.doi.org/10.1002/ange.200700834>
  • Prakash G. K. Surya, Chacko Sujith, Alconcel Steevens, Stewart Timothy, Mathew Thomas, Olah George A.: Stereoselective Monofluoromethylation of Primary and Secondary Alcohols by Using a Fluorocarbon Nucleophile in a Mitsunobu Reaction. Angew Chem Int Ed 2007, 46, 4933. <http://dx.doi.org/10.1002/anie.200700834>
  • Woo Grace H.C., Beeler Aaron B., Snyder John K.: 1,2,3,4-Tetrahydro-1,5-naphthyridines and related heterocyclic scaffolds: exploration of suitable chemistry for library development. Tetrahedron 2007, 63, 5649. <http://dx.doi.org/10.1016/j.tet.2007.04.003>
  • Véliz Eduardo A., Beal Peter A.: Mitsunobu reactions of nucleoside analogs using triisopropyl phosphite–DIAD. Tetrahetron Lett 2006, 47, 3153. <http://dx.doi.org/10.1016/j.tetlet.2006.02.138>
  • Sakamoto Izumi, Izumi Norimasa, Yamada Taeko, Tsunoda Tetsuto: 2-(1,3-Dioxan-2-yl)ethylsulfonyl Group:  A New Versatile Protecting and Activating Group for Amine Synthesis. Org Lett 2006, 8, 71. <http://dx.doi.org/10.1021/ol052545+>
  • Szabó Dénes, Bonto Ana-Maria, Kövesdi István, Gömöry Ágnes, Rábai József: Synthesis of novel lipophilic and/or fluorophilic ethers of perfluoro-tert-butyl alcohol, perfluoropinacol and hexafluoroacetone hydrate via a Mitsunobu reaction: Typical cases of ideal product separation. J FLUORINE CHEM 2005, 126, 639. <http://dx.doi.org/10.1016/j.jfluchem.2005.01.017>
  • Bálint Ana-Maria, Bodor Andrea, Gömöry Ágnes, Vékey Károly, Szabó Dénes, Rábai József: Mitsunobu synthesis of symmetrical alkyl and polyfluoroalkyl secondary amines. J FLUORINE CHEM 2005, 126, 1524. <http://dx.doi.org/10.1016/j.jfluchem.2005.08.012>
  • Dyck J., Zavorine S., Robertson A.J., Capretta A., Larichev V., Britten J., McNulty J.: Dimethylmalonyltrialkylphosphoranes: probing the steric effect on phosphorus and its stereochemical consequence in esterification reactions of chiral secondary alcohols. J Organomet Chem 2005, 690, 2548. <http://dx.doi.org/10.1016/j.jorganchem.2004.10.046>
  • Mukaiyama Teruaki, Aoki Hidenori: N-Alkylation of Phthalimide, Carboxamide, and Sulfonamides By Oxdation–Reduction Condensation Using Di-tert-butyl-1,4-benzoquinone and Alkyl Diphenylphosphinite. Chem Lett 2005, 34, 142. <http://dx.doi.org/10.1246/cl.2005.142>
  • Mukaiyama Teruaki, Nagata Yuzo, Ikegai Kazuhiro: Stereoselective Carbon–Carbon Bond Forming Reactions between Various Chiral Alkyl Aryl Carbinols and Triethyl Methanetricarboxylate by Oxidation–Reduction Condensation Using Alkyl Diphenylphosphinites. Chem Lett 2005, 34, 1676. <http://dx.doi.org/10.1246/cl.2005.1676>
  • Sakamoto Izumi, Nishii Takeshi, Ozaki Fumie, Kaku Hiroto, Tanaka Masami, Tsunoda Tetsuto: Preparation of (Cyanomethylene)tributylphosphorane: A New Mitsunobu-Type Reagent. Chem Pharm Bull 2005, 53, 1508. <http://dx.doi.org/10.1248/cpb.53.1508>
  • MUKAIYAMA Teruaki, IKEGAI Kazuhiro, AOKI Hidenori, PLUEMPANUPAT Wanchai, MASUTANI Kouta: New methods for carbon-nitrogen, carbon-sulfur, and carbon-carbon bond formations by quinone-mediated oxidation-reduction condensation using alkyl diphenylphosphinites. Proc Jpn Acad Ser B 2005, 81, 103. <http://dx.doi.org/10.2183/pjab.81.103>
  • Hillier Michael C., Desrosiers Jean-Nicolas, Marcoux Jean-François, Grabowski Edward J. J.: Stereoselective Carbon−Carbon Bond Formation via the Mitsunobu Displacement of Chiral Secondary Benzylic Alcohols. Org Lett 2004, 6, 573. <http://dx.doi.org/10.1021/ol036380l>
  • Kaku Hiroto, Okamoto Natsuko, Nakamaru Aya, Tsunoda Tetsuto: A Modified Thermodynamically Controlled Deracemization of 2-Allylcyclohexanone and Its Application to Asymmetric Synthesis of (R)-(−)-Epilachnene. Chem Lett 2004, 33, 516. <http://dx.doi.org/10.1246/cl.2004.516>
  • Seelen Werner, Schäfer Martina, Ernst Alexander: Selective ring N-protection of aminopyrazoles. Tetrahetron Lett 2003, 44, 4491. <http://dx.doi.org/10.1016/S0040-4039(03)00988-2>
  • Preparation of (Cyanomethylene)trimethylphosphorane as a New Mitsunobu-Type Reagent. Chem Pharm Bull 2003, 51, 474. <http://dx.doi.org/10.1248/cpb.51.474>
  • Bombrun Agnes, Casi Giulio: N-Alkylation of 1H-indoles and 9H-carbazoles with alcohols. Tetrahetron Lett 2002, 43, 2187. <http://dx.doi.org/10.1016/S0040-4039(02)00217-4>
  • Takacs James M., Xu Zhenrong, Jiang Xun-tian, Leonov Alexei P., Theriot Gregory C.: Carbon Nucleophiles in the Mitsunobu Reaction. Mono- and Dialkylation of Bis(2,2,2-trifluoroethyl) Malonates. Org Lett 2002, 4, 3843. <http://dx.doi.org/10.1021/ol0266626>
  • Falkiewicz Bogdan, Kołodziejczyk Aleksandra S, Liberek Bogdan, Wiśniewski Kazimierz: Synthesis of achiral and chiral peptide nucleic acid (PNA) monomers using Mitsunobu reaction. Tetrahedron 2001, 57, 7909. <http://dx.doi.org/10.1016/S0040-4020(01)00759-1>
  • ITÔ Shô: Development of New Synthetic Reagents in Mitsunobu-Type Reaction. YAKUGAKU ZASSHI 2001, 121, 567. <http://dx.doi.org/10.1248/yakushi.121.567>