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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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  • 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>
  • 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>
  • Wang Feijun, Liu Lian-jun, Wang Wenfeng, Li Shengke, Shi Min: Chiral NHC–metal-based asymmetric catalysis. Coord Rev 2011. <http://dx.doi.org/10.1016/j.ccr.2011.11.013>
  • 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>
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  • 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>