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Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 1025-1037

http://dx.doi.org/10.1351/pac200880051025

Copper-catalyzed asymmetric allylic substitution reactions with organozinc and Grignard reagents

Koen Geurts, Stephen P. Fletcher, Anthoni W. van Zijl, Adriaan J. Minnaard and Ben L. Feringa

Department of Organic Chemistry and Molecular Inorganic Chemistry,Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands

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  • Takeda Momotaro, Takatsu Keishi, Shintani Ryo, Hayashi Tamio: Synthesis of Quaternary Carbon Stereocenters by Copper-Catalyzed Asymmetric Allylic Substitution of Allyl Phosphates with Arylboronates. J. Org. Chem. 2014, 79, 2354. <http://dx.doi.org/10.1021/jo500068p>
  • Hornillos Valentín, Pérez Manuel, Fañanás-Mastral Martín, Feringa Ben L.: Copper-Catalyzed Enantioselective Allyl–Allyl Cross-Coupling. J. Am. Chem. Soc. 2013, 135, 2140. <http://dx.doi.org/10.1021/ja312487r>
  • Takeda Momotaro, Shintani Ryo, Hayashi Tamio: Enantioselective Synthesis of α-Tri- and α-Tetrasubstituted Allylsilanes by Copper-Catalyzed Asymmetric Allylic Substitution of Allyl Phosphates with Silylboronates. J. Org. Chem. 2013, 78, 5007. <http://dx.doi.org/10.1021/jo400888b>
  • Cui Xiaozhan, Wang Shulin, Zhang Yuwei, Deng Wei, Qian Qun, Gong Hegui: Nickel-catalyzed reductive allylation of aryl bromides with allylic acetates. Org. Biomol. Chem. 2013, 11, 3094. <http://dx.doi.org/10.1039/c3ob40232k>
  • Dai Yijing, Wu Fan, Zang Zhenhua, You Hengzhi, Gong Hegui: Ni-Catalyzed Reductive Allylation of Unactivated Alkyl Halides with Allylic Carbonates. Chemistry A European Journal 2012, 18, 808. <http://dx.doi.org/10.1002/chem.201102984>
  • Pérez Manuel, Fañanás-Mastral Martín, Hornillos Valentín, Rudolph Alena, Bos Pieter H., Harutyunyan Syuzanna R., Feringa Ben L.: Asymmetric Allylic Alkylation of Acyclic Allylic Ethers with Organolithium Reagents. Chem. Eur. J. 2012, 18, 11880. <http://dx.doi.org/10.1002/chem.201202251>
  • Wang Feijun, Liu Lian-jun, Wang Wenfeng, Li Shengke, Shi Min, M��ntym��ki Miia, Ritala Mikko, Leskel�� Markku: Chiral NHC���metal-based asymmetric catalysis. Coordination Chemistry Reviews 2012, 256, 804. <http://dx.doi.org/10.1016/j.ccr.2011.11.013>
  • Lölsberg Wibke, Werle Susen, Neudörfl Jörg-Martin, Schmalz Hans-Günther: An Enantioselective Total Synthesis of Helioporins C and E. Org. Lett. 2012, 14, 5996. <http://dx.doi.org/10.1021/ol302898h>
  • Tosatti Paolo, Nelson Adam, Marsden Stephen P.: Recent advances and applications of iridium-catalysed asymmetric allylic substitution. Biomol Chem 2012, 10, 3147. <http://dx.doi.org/10.1039/c2ob07086c>
  • Shintani Ryo, Takatsu Keishi, Takeda Momotaro, Hayashi Tamio: Copper-Catalyzed Asymmetric Allylic Substitution of Allyl Phosphates with Aryl- and Alkenylboronates. angew chemie 2011, 123, 8815. <http://dx.doi.org/10.1002/ange.201103581>
  • Shintani Ryo, Takatsu Keishi, Takeda Momotaro, Hayashi Tamio: Copper-Catalyzed Asymmetric Allylic Substitution of Allyl Phosphates with Aryl- and Alkenylboronates. Angew Chem Int E 2011, 50, 8656. <http://dx.doi.org/10.1002/anie.201103581>
  • Tosatti Paolo, Campbell Amanda J., House David, Nelson Adam, Marsden Stephen P.: Catalyst Control in Sequential Asymmetric Allylic Substitution: Stereodivergent Access to N,N-Diprotected Unnatural Amino Acids. J Org Chem 2011, 76, 5495. <http://dx.doi.org/10.1021/jo200720c>
  • den Hartog Tim, Maciá Beatriz, Minnaard Adriaan J., Feringa Ben L.: Copper-Catalyzed Asymmetric Allylic Alkylation of Halocrotonates: Efficient Synthesis of Versatile Chiral Multifunctional Building Blocks. Adv Synth Catal 2010, 352, 999. <http://dx.doi.org/10.1002/adsc.201000109>
  • Lölsberg Wibke, Ye Shute, Schmalz Hans-Günther: Enantioselective Copper-Catalysed Allylic Alkylation of Cinnamyl Chlorides by Grignard Reagents using Chiral Phosphine-Phosphite Ligands. Adv Synth Catal 2010, 352, 2023. <http://dx.doi.org/10.1002/adsc.201000213>
  • Teichert Johannes F., Feringa Ben L.: Phosphoramidites: Privileged Ligands in Asymmetric Catalysis. Angew Chem Int Ed 2010, 49, 2486. <http://dx.doi.org/10.1002/anie.200904948>
  • Šebesta Radovan, Škvorcová Andrea, Horváth Branislav: Asymmetric allylic substitutions on symmetrical and non-symmetrical substrates using [5]ferrocenophane ligands. Tet Asymm 2010, 21, 1910. <http://dx.doi.org/10.1016/j.tetasy.2010.05.054>
  • Okamoto Sentaro, Ishikawa Hiroyuki, Shibata Yoshimi, Suhara Yu-ichiro: Grignard allylic substitution catalyzed by imidazol-2-ylidene- and imidazol-4-ylidene-magnesium complexes. Tetrahetron Lett 2010, 51, 5704. <http://dx.doi.org/10.1016/j.tetlet.2010.08.067>
  • Han Xinping, Zhang Yanhua, Wu Jimmy: Mild Two-Step Process for the Transition-Metal-Free Synthesis of Carbon−Carbon Bonds from Allylic Alcohols/Ethers and Grignard Reagents. J Am Chem Soc 2010, 132, 4104. <http://dx.doi.org/10.1021/ja100747n>
  • Cannon Jeffrey S., Kirsch Stefan F., Overman Larry E.: Catalytic Asymmetric Synthesis of Chiral Allylic Esters. J Am Chem Soc 2010, 132, 15185. <http://dx.doi.org/10.1021/ja106685w>
  • Breuil Pierre-Alain R., Reek Joost N. H.: Amino Acid Based Phosphoramidite Ligands for the Rhodium-Catalyzed Asymmetric Hydrogenation. Eur J Org Chem 2009, 2009, 6225. <http://dx.doi.org/10.1002/ejoc.200901044>
  • Geurts Koen, Fletcher Stephen P., van Zijl Anthoni W., Minnaard Adriaan J., Feringa Ben L.: ChemInform Abstract: Copper-Catalyzed Asymmetric Allylic Substitution Reactions with Organozinc and Grignard Reagents. ChemInform 2008, 39. <http://dx.doi.org/10.1002/chin.200843241>