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Pure Appl. Chem., 1996, Vol. 68, No. 1, pp. 131-138

http://dx.doi.org/10.1351/pac199668010131

New developments in enantioselective hydrogenation

R. Schmid, E. A. Broger, Marco Cereghetti, Yvo Crameri, Joseph Foricher, M. Lalonde, R. K. Müller, M. Scalone, G. Schoettel and Ulrich Zutter

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  • Leseurre Lucie, Püntener Kurt, Genêt Jean-Pierre, Scalone Michelangelo, Michelet Véronique: Synthesis of New Water-Soluble Atropisomeric Ligands Derived from the MeOBIPHEP Skeleton: Applications for Asymmetric CH Bond Formation and Mechanistic Studies. Synth Catal 2011, 353, 3269. <http://dx.doi.org/10.1002/adsc.201100535>
  • Bantreil Xavier, Prestat Guillaume, Moreno Aitor, Madec David, Fristrup Peter, Norrby Per-Ola, Pregosin Paul S., Poli Giovanni: γ- and δ-Lactams through Palladium-Catalyzed Intramolecular Allylic Alkylation: Enantioselective Synthesis, NMR Investigation, and DFT Rationalization. Chem Eur J 2011, 17, 2885. <http://dx.doi.org/10.1002/chem.201001300>
  • Bonnafoux Laurence, Gramage-Doria Rafael, Colobert Françoise, Leroux Frédéric R.: Catalytic Palladium Phosphination: Modular Synthesis of C1-Symmetric Biaryl-Based Diphosphines. Chemistry A European Journal 2011, 17, 11008. <http://dx.doi.org/10.1002/chem.201101529>
  • Yu Feng, Zhou Ji-Ning, Zhang Xi-Chang, Sui Yao-Zong, Wu Fei-Fei, Xie Lin-Jie, S. C. Chan Albert, Wu Jing: Copper(II)-Catalyzed Hydrosilylation of Ketones Using Chiral Dipyridylphosphane Ligands: Highly Enantioselective Synthesis of Valuable Alcohols. Chemistry A European Journal 2011, 17, 14234. <http://dx.doi.org/10.1002/chem.201102157>
  • Voigtritter Karl R., Isley Nicholas A., Moser Ralph, Aue Donald H., Lipshutz Bruce H.: Regioselective reductions of β,β-disubstituted enones catalyzed by nonracemically ligated copper hydride. Tedrahedron 2011. <http://dx.doi.org/10.1016/j.tet.2011.10.056>
  • Le Boucher d’Herouville Florent, Millet Anthony, Scalone Michelangelo, Michelet Véronique: Room-Temperature Rh-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to Maleimides and Enones in the Presence of CF3-Substituted MeOBIPHEP Analogues. J Org Chern 2011, 76, 6925. <http://dx.doi.org/10.1021/jo201073y>
  • Knight John D., Sauer Scott J., Coltart Don M.: Asymmetric Total Synthesis of the Antimalarial Drug (+)-Mefloquine Hydrochloride via Chiral N-Amino Cyclic Carbamate Hydrazones. Org Lett 2011, 13, 3118. <http://dx.doi.org/10.1021/ol2010193>
  • Leseurre Lucie, Le Boucher d’Herouville Florent, Püntener Kurt, Scalone Michelangelo, Genêt Jean-Pierre, Michelet Véronique: Efficient Route to Atropisomeric Ligands – Application to the Synthesis of MeOBIPHEP Analogues. Org Lett 2011, 13, 3250. <http://dx.doi.org/10.1021/ol2011874>
  • Wu Zi, Ayad Tahar, Ratovelomanana-Vidal Virginie: Efficient Enantioselective Synthesis of 3-Aminochroman Derivatives Through Ruthenium-Synphos Catalyzed Asymmetric Hydrogenation. Org Lett 2011, 13, 3782. <http://dx.doi.org/10.1021/ol201786q>
  • Goto Mitsutaka, Konishi Takahiro, Kawaguchi Shinji, Yamada Masatoshi, Nagata Toshiaki, Yamano Mitsuhisa: Process Research on the Asymmetric Hydrogenation of a Benzophenone for Developing the Manufacturing Process of the Squalene Synthase Inhibitor TAK-475. Org Process Res Dev 2011, 110826103456057. <http://dx.doi.org/10.1021/op2001673>
  • Kim Dong Eun, Ratovelomanana-Vidal Virginie, Jeong Nakcheol: 2,2′-Bis[bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-6,6′-dimethoxy-1,1′-biphenyl in Intramolecular Rhodium(I)-Catalyzed Asymmetric Pauson-Khand-Type Reactions. Adv Synth Catal 2010, 352, 2032. <http://dx.doi.org/10.1002/adsc.201000221>
  • Wang Changqing, Yang Guoqiang, Zhuang Jing, Zhang Wanbin: From tropos to atropos: 5,5′-bridged 2,2′-bis(diphenylphosphino)biphenyls as chiral ligands for highly enantioselective palladium-catalyzed hydrogenation of α-phthalimide ketones. Tetrahetron Lett 2010, 51, 2044. <http://dx.doi.org/10.1016/j.tetlet.2010.02.055>
  • Moser Ralph, Bošković Žarko V., Crowe Christopher S., Lipshutz Bruce H.: CuH-Catalyzed Enantioselective 1,2-Reductions of α,β-Unsaturated Ketones. J Am Chem Soc 2010, 132, 7852. <http://dx.doi.org/10.1021/ja102689e>
  • PENG Zonghai, MA Menglin, FU Haiyan, CHEN Hua, LI Xianjun: β-Ketoesters Catalyzed by Ru Complex with Para-alkoxy Substituted MeO-BIPHEP Type Diphosphine Ligands]]> : Asymmetric Hydrogenation of β-Ketoesters Catalyzed by Ru Complex with Para-alkoxy Substituted MeO-BIPHEP Type Diphosphine Ligands. CHINESE JOURNAL OF CATALYSIS (CHINESE VERSION) 2010, 31, 191. <http://dx.doi.org/10.3724/SP.J.1088.2010.90737>
  • Sun Xianfeng, Li Wei, Hou Guohua, Zhou Le, Zhang Xumu: Axial Chirality Control by 2,4-Pentanediol for the Alternative Synthesis of C3*-TunePhos Chiral Diphosphine Ligands and Their Applications in Highly Enantioselective Ruthenium-Catalyzed Hydrogenation of ��-Keto Esters. Adv Synth Catal 2009, 351, 2553. <http://dx.doi.org/10.1002/adsc.200900589>
  • Chao Chung-Meng, Vitale Maxime R., Toullec Patrick Y., Genêt Jean-Pierre, Michelet Véronique: Asymmetric Gold-Catalyzed Hydroarylation/Cyclization Reactions. Chem Eur J 2009, 15, 1319. <http://dx.doi.org/10.1002/chem.200802341>
  • Chao Chung-Meng, Genin Emilie, Toullec Patrick Y., Genêt Jean-Pierre, Michelet Véronique: Towards asymmetric Au-catalyzed hydroxy- and alkoxycyclization of 1,6-enynes. J Organomet Chem 2009, 694, 538. <http://dx.doi.org/10.1016/j.jorganchem.2008.08.008>
  • Wang Chun-Jiang, Wang Chu-Bei, Chen Dong, Yang Guangfu, Wu Zhengshun, Zhang Xumu: Axially 4,4′-di-tert-butyl TunePhos-type chiral diphosphine ligand: synthesis and applications in asymmetric hydrogenation. Tetrahetron Lett 2009, 50, 1038. <http://dx.doi.org/10.1016/j.tetlet.2008.12.057>
  • Mino Takashi, Naruse Yoshiaki, Kobayashi Shohei, Oishi Shunsuke, Sakamoto Masami, Fujita Tsutomu: Synthesis and application of atropisomeric dihydrobenzofuran-based bisphosphine (BICMAP). Tetrahetron Lett 2009, 50, 2239. <http://dx.doi.org/10.1016/j.tetlet.2009.02.182>
  • Zou Yaping, Geng Huiling, Zhang Weicheng, Yu Shichao, Zhang Xumu: Axially chiral electron-rich TunePhos-type ligand: synthesis and applications in asymmetric hydrogenation. Tetrahetron Lett 2009, 50, 5777. <http://dx.doi.org/10.1016/j.tetlet.2009.07.007>
  • Chao Chung-Meng, Beltrami Denis, Toullec Patrick Y., Michelet Véronique: Asymmetric Au(i)-catalyzed synthesis of bicyclo[4.1.0]heptene derivatives via a cycloisomerization process of 1,6-enynes. Chem Commun 2009, 6988. <http://dx.doi.org/10.1039/b913554e>
  • Pautigny Cyrielle, Jeulin Séverine, Ayad Tahar, Zhang Zhaoguo, Genêt Jean-Pierre, Ratovelomanana-Vidal Virginie: Convenient General Asymmetric Synthesis of Roche Ester Derivatives through Catalytic Asymmetric Hydrogenation: Steric and Electronic Effects of Ligands. Adv Synth Catal 2008, 350, 2525. <http://dx.doi.org/10.1002/adsc.200800504>
  • Kesselgruber Martin, Lotz Matthias, Martin Pierre, Melone Gianpietro, Müller Markus, Pugin Benoît, Naud Frédéric, Spindler Felix, Thommen Marc, Zbinden Paul: Solphos: A New Family of Efficient Biaryl Diphosphine Ligands. Chem Asian J 2008, 3, 1384. <http://dx.doi.org/10.1002/asia.200800186>
  • Ohshima Takashi, Tadaoka Hiroshi, Hori Kiyoto, Sayo Noboru, Mashima Kazushi: Highly Enantio- and s-trans CC Bond Selective Catalytic Hydrogenation of Cyclic Enones: Alternative Synthesis of (−)-Menthol. Chem Eur J 2008, 14, 2060. <http://dx.doi.org/10.1002/chem.200701505>
  • XIE Zhi-Xiang, ZHANG Lu-Zhong, REN Xiao-Juan, TANG Shi-Yang, LI Ying: Asymmetric Synthesis of (+)-(11R,12S)-MefloquineHydrochloride . Chin J Chem 2008, 26, 1272. <http://dx.doi.org/10.1002/cjoc.200890231>
  • ZHANG Hong-Wei, MENG Qing-Hua, ZHANG Zhao-Guo: Synthesis of Enantiopure SunPhos Diphosphine and Its Reaction with Methyl Acrylate. Chin J Chem 2008, 26, 2098. <http://dx.doi.org/10.1002/cjoc.200890374>
  • Wei Hao, Zhang Yong Jian, Wang Feijun, Zhang Wanbin: Novel atropisomeric bisphosphine ligands with a bridge across the 5,5′-position of the biphenyl for asymmetric catalysis. Tet Asymm 2008, 19, 482. <http://dx.doi.org/10.1016/j.tetasy.2008.01.023>
  • Cesarotti Edoardo, Abbiati Giorgio, Rossi Elisabetta, Spalluto Paola, Rimoldi Isabella: DIOPHEP, a chiral diastereoisomeric bisphosphine ligand: synthesis and applications in asymmetric hydrogenations. Tet Asymm 2008, 19, 1654. <http://dx.doi.org/10.1016/j.tetasy.2008.07.009>
  • Wei Hao, Zhang Yong Jian, Dai Yijun, Zhang Jiaming, Zhang Wanbin: Novel atropisomeric aminophosphine ligands with a bridge across the 5,5′-position of biphenyl for Rh(I)-catalyzed asymmetric hydrogenation. Tetrahetron Lett 2008, 49, 4106. <http://dx.doi.org/10.1016/j.tetlet.2008.04.140>
  • Leroux Frédéric R., Mettler Hanspeter: First Modular Synthesis of Dissymmetric Biaryldiphosphine Ligands Allowing Tunable Steric and Electronic Effects. Adv Synth Catal 2007, 349, 323. <http://dx.doi.org/10.1002/adsc.200600300>
  • Schmidt Frank, Rudolph Jens, Bolm Carsten: Diarylmethanols by Catalyzed Asymmetric Aryl Transfer Reactions onto Aldehydes Using Boronic Acids as Aryl Source. Adv Synth Catal 2007, 349, 703. <http://dx.doi.org/10.1002/adsc.200600390>
  • Chai Li-Ting, Wang Wei-Wei, Wang Quan-Rui, Tao Feng-Gang: Asymmetric hydrogenation of aromatic ketones with MeO-PEG-supported BIPHEP/DPEN ruthenium catalysts. Journal of Molecular Catalysis A 2007, 270, 83. <http://dx.doi.org/10.1016/j.molcata.2007.01.042>
  • Alamé M., Jahjah M., Pellet-Rostaing S., Lemaire M., Meille V., de Bellefon C.: 2,2′-Bis-[bis(4-substituted-phenyl)phosphino]-1,1′-binaphthyl derivatives in Rh(I)-catalyzed hydrogenation of acetamidoacrylic acid derivatives: Electronic effects. Journal of Molecular Catalysis A 2007, 271, 18. <http://dx.doi.org/10.1016/j.molcata.2007.02.027>
  • Cesarotti Edoardo, Rimoldi Isabella, Spalluto Paola, Demartin Francesco: Chiral 1,4-bis-diphosphine ligands from optically active (Z)-olefines. Tet Asymm 2007, 18, 1278. <http://dx.doi.org/10.1016/j.tetasy.2007.04.018>
  • Schmitkamp Mike, Chen Dianjun, Leitner Walter, Klankermayer Jürgen, Franciò Giancarlo: Enantioselective catalysis with tropos ligands in chiral ionic liquids. Chem Commun 2007, 4012. <http://dx.doi.org/10.1039/b712068k>
  • Lipshutz Bruce H., Frieman Bryan A., Tomaso Anthony E.: Copper-in-Charcoal (Cu/C): Heterogeneous, Copper-Catalyzed Asymmetric Hydrosilylations. Angew Chem 2006, 118, 1281. <http://dx.doi.org/10.1002/ange.200503149>
  • Hiney Rachel M., Higham Lee J., Müller-Bunz Helge, Gilheany Declan G.: Taming a Functional Group: Creating Air-Stable, Chiral Primary Phosphanes. Angew Chem 2006, 118, 7406. <http://dx.doi.org/10.1002/ange.200602143>
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  • Hiney Rachel M., Higham Lee J., Müller-Bunz Helge, Gilheany Declan G.: Taming a Functional Group: Creating Air-Stable, Chiral Primary Phosphanes. Angew Chem Int Ed 2006, 45, 7248. <http://dx.doi.org/10.1002/anie.200602143>
  • Guo Yu, Chen Hua, Li Xian-Jun, Ma Meng-Lin, Peng Zong-Hai, Chen Li: Synthesis of New MeO-BIPHEP-type Chiral Diphosphines by an Improved Way. Chin J Chem 2006, 24, 1391. <http://dx.doi.org/10.1002/cjoc.200690260>
  • Flanagan Susan P., Guiry Patrick J.: Substituent electronic effects in chiral ligands for asymmetric catalysis. J Organomet Chem 2006, 691, 2125. <http://dx.doi.org/10.1016/j.jorganchem.2006.01.063>
  • Deng Guo-Jun, Li Guo-Rui, Zhu Ling-Yun, Zhou Hai-Feng, He Yan-Mei, Fan Qing-Hua, Shuai Zhi-Gang: Dendritic BIPHEP: Synthesis and application in asymmetric hydrogenation of β-ketoesters. Journal of Molecular Catalysis A 2006, 244, 118. <http://dx.doi.org/10.1016/j.molcata.2005.08.036>
  • Lipshutz Bruce H., Lower Asher, Kucejko Robert J., Noson Kevin: Applications of Asymmetric Hydrosilylations Mediated by Catalytic (DTBM-SEGPHOS)CuH. Org Lett 2006, 8, 2969. <http://dx.doi.org/10.1021/ol060854+>
  • Han Xiaoqing, Widenhoefer Ross A.: Platinum-Catalyzed Intramolecular Asymmetric Hydroarylation of Unactivated Alkenes with Indoles. Org Lett 2006, 8, 3801. <http://dx.doi.org/10.1021/ol061441b>
  • Bonrath Werner, Netscher Thomas: Catalytic processes in vitamins synthesis and production. CATAL A GENERAL 2005, 280, 55. <http://dx.doi.org/10.1016/j.apcata.2004.08.028>
  • Raghunath Malati, Zhang Xumu: A correlation study of bisphosphine ligand bite angles with enantioselectivity in Pd-catalyzed asymmetric transformations. Tetrahetron Lett 2005, 46, 8213. <http://dx.doi.org/10.1016/j.tetlet.2005.09.093>
  • Suto Yutaka, Tsuji Riichiro, Kanai Motomu, Shibasaki Masakatsu: Cu(I)-Catalyzed Direct Enantioselective Cross Aldol-Type Reaction of Acetonitrile. Org Lett 2005, 7, 3757. <http://dx.doi.org/10.1021/ol051423e>
  • Lam Hon Wai, Joensuu Pekka M.: Cu(I)-Catalyzed Reductive Aldol Cyclizations:  Diastereo- and Enantioselective Synthesis of β-Hydroxylactones. Org Lett 2005, 7, 4225. <http://dx.doi.org/10.1021/ol051649h>
  • Lipshutz Bruce H, Frieman Bryan A, Unger John B, Nihan Danielle M: Thermally accelerated asymmetric hydrosilylations using ligated copper hydride. Can J Chem 2005, 83, 606. <http://dx.doi.org/10.1139/v05-083>
  • Rojo Isabel, Teixidor Francesc, Viñas Clara, Kivekäs Raikko, Sillanpää Reijo: Synthesis and Coordinating Ability of an Anionic Cobaltabisdicarbollide Ligand Geometrically Analogous to BINAP. Chem Eur J 2004, 10, 5376. <http://dx.doi.org/10.1002/chem.200400361>
  • Singh Sanjay K, Chandra Manish, Pandey Daya S: Ru(II) complexes imparting N2O2 donor bis chelating ligand N,N′-bis(salicylidine)-hydrazine in unusual coordination mode. J Organomet Chem 2004, 689, 2073. <http://dx.doi.org/10.1016/j.jorganchem.2004.03.031>
  • Sı́pos É., Tungler A., Fogassy G.: New substrates and modifiers in the enantioselective heterogeneous catalytic hydrogenation of the CC double bond. Journal of Molecular Catalysis A 2004, 216, 171. <http://dx.doi.org/10.1016/j.molcata.2004.03.018>
  • Herseczki Zsanett, Gergely Ildikó, Hegedüs Csaba, Szöllősy Áron, Bakos József: Electronic and steric effects of ligands as control elements for rhodium-catalyzed asymmetric hydrogenation. Tet Asymm 2004, 15, 1673. <http://dx.doi.org/10.1016/j.tetasy.2004.04.023>
  • Sun Yanhui, Wan Xiaobing, Guo Minjie, Wang Donghui, Dong Xicheng, Pan Yi, Zhang Zhaoguo: Chiral biphosphine ligands for the Ru-catalyzed enantioselective hydrogenation of β-ketoesters. Tet Asymm 2004, 15, 2185. <http://dx.doi.org/10.1016/j.tetasy.2004.04.034>
  • Steiner Ivo, Aufdenblatten Rhony, Togni Antonio, Blaser Hans-Ulrich, Pugin Benoı̂t: Novel silica gel supported chiral biaryl-diphosphine ligands for enantioselective hydrogenation. Tet Asymm 2004, 15, 2307. <http://dx.doi.org/10.1016/j.tetasy.2004.05.003>
  • Shimizu Hideo, Ishizaki Takero, Fujiwara Takahiro, Saito Takao: A novel approach for investigating enantioselectivity in asymmetric hydrogenation. Tet Asymm 2004, 15, 2169. <http://dx.doi.org/10.1016/j.tetasy.2004.05.028>
  • Wu Shulin, He Minsheng, Zhang Xumu: Synthesis of ortho-phenyl substituted MeO-BIPHEP ligand and its application in Rh-catalyzed asymmetric hydrogenation. Tet Asymm 2004, 15, 2177. <http://dx.doi.org/10.1016/j.tetasy.2004.05.043>
  • Lipshutz Bruce H., Servesko Jeff M., Petersen Tue B., Papa Patrick P., Lover Andrew A.: Asymmetric 1,4-Reductions of Hindered β-Substituted Cycloalkenones Using Catalytic SEGPHOS−Ligated CuH. Org Lett 2004, 6, 1273. <http://dx.doi.org/10.1021/ol0400185>
  • Duprat de Paule Sébastien, Jeulin Séverine, Ratovelomanana-Vidal Virginie, Genêt Jean-Pierre, Champion Nicolas, Dellis Philippe: SYNPHOS®, a new chiral diphosphine ligand: synthesis, molecular modeling and application in asymmetric hydrogenation. Tetrahetron Lett 2003, 44, 823. <http://dx.doi.org/10.1016/S0040-4039(02)02637-0>
  • Lipshutz Bruce H., Caires Christopher C., Kuipers Peter, Chrisman Will: Tweaking Copper Hydride (CuH) for Synthetic Gain. A Practical, One-Pot Conversion of Dialkyl Ketones to Reduced Trialkylsilyl Ether Derivatives. Org Lett 2003, 5, 3085. <http://dx.doi.org/10.1021/ol035164+>
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  • Lipshutz Bruce H., Lower Asher, Noson Kevin: Copper(I) Hydride-Catalyzed Asymmetric Hydrosilylation of Heteroaromatic Ketones. Org Lett 2002, 4, 4045. <http://dx.doi.org/10.1021/ol026755n>
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