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Pure Appl. Chem., 2006, Vol. 78, No. 2, pp. 477-494

Acid-base catalysis using chiral palladium complexes

Mikiko Sodeoka1,2 and Yoshitaka Hamashima1

1 Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, Katahira, Aoba, Miyagi 980-8577, Japan
2 RIKEN (The Institute of Physical and Chemical Research), Hirosawa, Wako, Saitama 351-0198, Japan

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  • Sun Yin-wei, Zhu Peng-long, Xu Qin, Shi Min: Development of Pd catalyzed asymmetric additions in the last five years. RSC Adv. 2013, 3, 3153. <>
  • Nayab Saira, Lee Hong-In, Jeong Jong Hwa: Dichlorido{2,6-diisopropyl-N-[(S)-pyrrolidin-2-ylmethyl]aniline-κ2N,N′}palladium(II). Acta Crystallogr E Struct Rep Online 2013, 69, m238. <>
  • Hamashima Yoshitaka, Suzuki Shoko, Tamura Toshihiro, Somei Hidenori, Sodeoka Mikiko: Scope and Mechanism of Tandem Aza-Michael Reaction/Enantioselective Protonation Using a Pd-μ-Hydroxo Complex under Mild Conditions Buffered with Amine Salts. Chem Asian J 2011, 6, 658. <>
  • Santana M. Dolores, García-Bueno Rocío, García Gabriel, Sánchez Gregorio, García Joaquín, Pérez José, García Luis, Serrano J. Luis: Luminescence properties of cyclopalladated complexes with Schiff base ligands. Inorg Chim Ada 2011, 378, 49. <>
  • Serrano José Luis, García Luis, Pérez José, Pérez Eduardo, Galiana José Miguel, García Joaquín, Martínez Marina, Sánchez Gregorio, Silva Ivan da: New cyclometallated precursors of unsubstituted N-phenylpyrazole [{Pd(phpz)(μ-X)}2] (X = AcO or OH) and study of their reactivity towards selected ligands. Dalton Trans 2011, 40, 156. <>
  • Hamashima Yoshitaka, Sodeoka Mikiko: Development of Novel Asymmetric Reactions Based on Acid-base Catalysis of Late Transition Metal Complexes. J Syn Org Chem Jpn 2011, 69, 972. <>
  • Nakamura Ayako, Lectard Sylvain, Shimizu Ryo, Hamashima Yoshitaka, Sodeoka Mikiko: Asymmetric conjugate addition of α-keto esters to nitroolefins catalyzed by chiral CuII hydroxo complexes. Tet Asymm 2010, 21, 1682. <>
  • Ebner David C., Bagdanoff Jeffrey T., Ferreira Eric M., McFadden Ryan M., Caspi Daniel D., Trend Raissa M., Stoltz Brian M.: The Palladium-Catalyzed Aerobic Kinetic Resolution of Secondary Alcohols: Reaction Development, Scope, and Applications. Chem Eur J 2009, 15, 12978. <>
  • Xiao Yuanjing, Zhang Junliang: Furans versus 4H-pyrans: catalyst-controlled regiodivergent tandem Michael addition–cyclization reaction of 2-(1-alkynyl)-2-alken-1-ones with 1,3-dicarbonyl compounds. Chem Commun 2009, 3594. <>
  • Sodeoka Mikiko, Hamashima Yoshitaka: Chiral Pd aqua complex-catalyzed asymmetric C–C bond-forming reactions: a Brønsted acid–base cooperative system. Chem Commun 2009, 5787. <>
  • Umebayashi Natsuko, Hamashima Yoshitaka, Hashizume Daisuke, Sodeoka Mikiko: Catalytic Enantioselective Aldol-type Reaction of β-Ketosters with Acetals. Angew Chem 2008, 120, 4264. <>
  • Umebayashi Natsuko, Hamashima Yoshitaka, Hashizume Daisuke, Sodeoka Mikiko: Catalytic Enantioselective Aldol-type Reaction of β-Ketosters with Acetals. Angew Chem Int Ed 2008, 47, 4196. <>
  • Hamashima Yoshitaka, Sasamoto Naoki, Umebayashi Natsuko, Sodeoka Mikiko: PdII-Catalyzed Asymmetric Addition Reactions of 1,3-Dicarbonyl Compounds: Mannich-Type Reactions with N-Boc Imines and Three-Component Aminomethylation. Chem Asian J 2008, 3, 1443. <>
  • Muñiz Kilian, Streuff Jan, Chávez Patricia, Hövelmann Claas H.: Synthesis of Diamino Carboxylic Esters by Palladium-Catalyzed Oxidative Intramolecular Diamination of Acrylates. Chem Asian J 2008, 3, 1248. <>
  • Serrano José Luis, García Luis, Pérez José, Pérez Eduardo, García Joaquín, Sánchez Gregorio, López Gregorio, Liu Malva: Reactivity Towards Acidic Protic Ligands of Cyclopalladated Di-μ-hydroxo Complexes. Eur J Inorg Chem 2008, 2008, 4797. <>
  • Monguchi Daiki, Beemelmanns Christine, Hashizume Daisuke, Hamashima Yoshitaka, Sodeoka Mikiko: Catalytic asymmetric conjugate reduction with ethanol: A more reactive system Pd(II)–iPr-DUPHOS complex with molecular sieves 4A. J Organomet Chem 2008, 693, 867. <>
  • Zalevskaya O. A., Vorob’eva E. G., Dvornikova I. A., Kuchin A. V.: Palladium complexes based on optically active terpene derivatives of ethylenediamine. RUCO 2008, 34, 855. <>
  • Maya Celia M., Cámpora Juan, Carmona Ernesto, Matas Inmaculada, Palma Pilar, Gutiérrez-Puebla Enrique, Monge Angeles: Conjugate Additions of Cyclic Oxygen-Bound Nickel Enolates to α,β-Unsaturated Ketones. Chem Eur J 2007, 13, 3675. <>
  • Sodeoka Mikiko, Hamashima Yoshitaka: Acid—Base Catalysis Using Chiral Palladium Complexes. ChemInform 2006, 37. <>
  • Tsuchiya Yasunori, Hamashima Yoshitaka, Sodeoka Mikiko: A New Entry to Pd−H Chemistry:  Catalytic Asymmetric Conjugate Reduction of Enones with EtOH and a Highly Enantioselective Synthesis of Warfarin. Org Lett 2006, 8, 4851. <>