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Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 1109-1113

http://dx.doi.org/10.1351/pac200880051109

Asymmetric synthesis of planar-chiral ferrocenes by Mo- or Ru-catalyzed enantioselective metathesis

Masamichi Ogasawara1, Susumu Watanabe1, Kiyohiko Nakajima2 and Tamotsu Takahashi1

1 Catalysis Research Center and Graduate School of Life Science, Hokkaido University, and SORST, Japan Science and Technology Agency (JST), Kita-ku, Sapporo 001-0021, Japan
2 Department of Chemistry, Aichi University of Education, Igaya, Kariya 448-8542, Japan

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  • Gao De-Wei, Yin Qin, Gu Qing, You Shu-Li: Enantioselective Synthesis of Planar Chiral Ferrocenes via Pd(0)-Catalyzed Intramolecular Direct C–H Bond Arylation. J. Am. Chem. Soc. 2014, 136, 4841. <http://dx.doi.org/10.1021/ja500444v>
  • Ogasawara Masamichi, Arae Sachie, Watanabe Susumu, Nakajima Kiyohiko, Takahashi Tamotsu: Kinetic Resolution of Planar-Chiral 1,2-Disubstituted Ferrocenes by Molybdenum-Catalyzed Asymmetric Intraannular Ring-Closing Metathesis. Chem. Eur. J. 2013, 19, 4151. <http://dx.doi.org/10.1002/chem.201300116>
  • Gao De-Wei, Shi Yan-Chao, Gu Qing, Zhao Zheng-Le, You Shu-Li: Enantioselective Synthesis of Planar Chiral Ferrocenes via Palladium-Catalyzed Direct Coupling with Arylboronic Acids. J. Am. Chem. Soc. 2013, 135, 86. <http://dx.doi.org/10.1021/ja311082u>
  • Schaarschmidt Dieter, Lang Heinrich: Selective Syntheses of Planar-Chiral Ferrocenes. Organometallics 2013, 32, 5668. <http://dx.doi.org/10.1021/om400564x>
  • Ogasawara Masamichi, Wu Wei-Yi, Arae Sachie, Nakajima Kiyohiko, Takahashi Tamotsu: Inter- versus Intraannular Ring-Closing Metathesis of Polyallylferrocenes: Five-Fold RCM within a Single Molecule. Organometallics 2013, 32, 6593. <http://dx.doi.org/10.1021/om400936b>
  • Pi Chao, Li Ying, Cui Xiuling, Zhang Hao, Han Yanbing, Wu Yangjie: Redox of ferrocene controlled asymmetric dehydrogenative Heck reaction via palladium-catalyzed dual C–H bond activation. Chem. Sci. 2013, 4, 2675. <http://dx.doi.org/10.1039/c3sc50577d>
  • Ogasawara Masamichi, Wu Wei-Yi, Arae Sachie, Watanabe Susumu, Morita Tomotaka, Takahashi Tamotsu, Kamikawa Ken: Kinetic Resolution of Planar-Chiral (η6 -Arene)Chromium Complexes by Molybdenum-Catalyzed Asymmetric Ring-Closing Metathesis. Angew. Chem. 2012, 124, 3005. <http://dx.doi.org/10.1002/ange.201108292>
  • Ogasawara Masamichi, Wu Wei-Yi, Arae Sachie, Watanabe Susumu, Morita Tomotaka, Takahashi Tamotsu, Kamikawa Ken: Kinetic Resolution of Planar-Chiral (η6 -Arene)Chromium Complexes by Molybdenum-Catalyzed Asymmetric Ring-Closing Metathesis. Angew. Chem. Int. Ed. 2012, 51, 2951. <http://dx.doi.org/10.1002/anie.201108292>
  • Pellissier Hélène: Catalytic Non-Enzymatic Kinetic Resolution. Synth Catal 2011, 353, 1613. <http://dx.doi.org/10.1002/adsc.201100111>
  • Ogasawara Masamichi, Wu Wei-Yi, Arae Sachie, Morita Tomotaka, Watanabe Susumu, Takahashi Tamotsu, Kamikawa Ken: Ring-closing metathesis within chromium-coordination sphere: Facile access to phosphine-chelate (π-arene)chromium complexes. J Organomet Chem 2011, 696, 3987. <http://dx.doi.org/10.1016/j.jorganchem.2011.05.006>
  • Latorre Alfonso, Urbano Antonio, Carmen Carreño M.: Synthesis and chiroptical properties of ferrocene-[4]-helicenequinones: kinetic resolution of a planar-chiral diene. Chemical Communication 2011, 47, 8103. <http://dx.doi.org/10.1039/c1cc12921j>
  • Herndon James W.: The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2008. Coord Chem Rev - 2010, 254, 103. <http://dx.doi.org/10.1016/j.ccr.2009.07.018>
  • Patti Angela, Pedotti Sonia: Parallel or classical kinetic resolution of a planar chiral ferrocenylketone through asymmetric reductions. Tet Asymm 2010, 21, 2631. <http://dx.doi.org/10.1016/j.tetasy.2010.10.004>
  • Ogasawara Masamichi, Watanabe Susumu, Nakajima Kiyohiko, Takahashi Tamotsu: Enantioselective Synthesis of Planar-Chiral Phosphaferrocenes by Molybdenum-Catalyzed Asymmetric Interannular Ring-Closing Metathesis. J Am Chem Soc 2010, 132, 2136. <http://dx.doi.org/10.1021/ja910348z>
  • Alba Andrea-Nekane, Gómez-Sal Pilar, Rios Ramon, Moyano Albert: Organocatalytic kinetic resolution of a planar-chiral ferrocenecarbaldehyde. Tet Asymm 2009, 20, 1314. <http://dx.doi.org/10.1016/j.tetasy.2009.05.011>
  • Mercier Audrey, Yeo Wee Chuan, Chou Jingyu, Chaudhuri Piyali Datta, Bernardinelli Gérald, Kündig E. Peter: Synthesis of highly enantiomerically enriched planar chiral ruthenium complexes via Pd-catalysed asymmetric hydrogenolysis. Chem Commun 2009, 5227. <http://dx.doi.org/10.1039/b910977c>
  • Lee Woo-Jin, Chea Jong-Myoung, Jahng Yurng-Dong: Synthesis of Heteroarylferrocenes by FriedlanderReaction and Their Spectral Properties. Bulletin of the Korean Chemical Society 2009, 30, 3061. <http://dx.doi.org/10.5012/bkcs.2009.30.12.3061>
  • Ogasawara Masamichi, Watanabe Susumu, Nakajima Kiyohiko, Takahashi Tamotsu: ChemInform Abstract: Asymmetric Synthesis of Planar-Chiral Ferrocenes by Mo- or Ru-Catalyzed Enantioselective Metathesis. ChemInform 2008, 39. <http://dx.doi.org/10.1002/chin.200840217>