Recent Advances in Asymmetric Synthesis of Р -Stereogenic Phosphorus Compounds
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  • 关键词:Asymmetric catalysis ; Asymmetric synthesis ; Biocatalysis ; Ephedrine ; P ; Chiral phosphorus compounds ; Sparteine
  • 刊名:Topics in Current Chemistry
  • 出版年:2015
  • 出版时间:2015
  • 年:2015
  • 卷:360
  • 期:1
  • 页码:161-236
  • 全文大小:6,372 KB
  • 参考文献:1. Darcel C, Uziel J, Jugé S (2008) In: B?rner A (ed) Phosphorus ligands in asymmetric catalysis, vol 3. Wiley-VCH, Weinheim, pp 1211-233
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    3. Harvey, JS, Gouverneur, V (2010) Catalytic enantioselective synthesis of P-stereogenic compounds. J Chem Soc Chem Commun 46: pp. 7477-7485
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    5. Bayardon, J, Juge, S P-Chiral ligands. In: Kamer, PCJ, Leeuwen, PWNM eds. (2012) Phosphorus(III) ligands in homogeneous catalysis: design and synthesis. Wiley, Hoboken, pp. 355-389
    6. Kolodiazhnyi, OI (2012) Recent developments in the asymmetric synthesis of P-chiral phosphorus compounds. Tetrahedron Asymmetry 23: pp. 1-46
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    12. Gatineau, D, Giordano, L, Buono, G (2011) Bulky, optically active P-stereogenic phosphineboranes from pure H-menthylphosphinates. J Am Chem Soc 133: pp. 10728-10731
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    16. Humbel, S, Bertrand, C, Darcel, C, Bauduin, C, Jugé, S (2003) Configurational stability of chlorophosphines. Inorg Chem 42: pp. 420-427
    17. Hayakawa Y, Hyodo M, Kimura K, Kataoka M (2003) The first asymmetric synthesis of trialkyl phosphates on the basis of dynamic kinetic resolution in the phosphite method using a chiral source in a catalytic manner. J Chem Soc Chem Commun pp 1704-705
    18. Reichl, KD, Ess, DH, Radosevich, AT (2013) Catalyzing pyramidal inversion: configurational lability of P-stereogenic phosphines via single electron oxidation. J Am Chem Soc 135: pp. 9354-9357
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  • 作者单位:Phosphorus Chemistry I
  • 丛书名:978-3-319-15472-5
  • 刊物类别:Chemistry and Materials Science
  • 刊物主题:Chemistry
    Organic Chemistry
    Inorganic Chemistry
    Theoretical and Computational Chemistry
    Medicinal Chemistry
    Biochemistry
    Organometallic Chemistry
  • 出版者:Springer Berlin / Heidelberg
  • ISSN:1436-5049
文摘
This chapter points out significant advances in the asymmetric synthesis of P-chiral organophosphorus compounds with many applications in stereoselective synthesis and in asymmetric catalysis, making reference to updated literature findings as well as the author’s original research. Asymmetric addition and cycloaddition reactions, oxidation, including metal catalyzed and non-metal biocatalytic methods are described, in addition to synthetic approaches via nucleophilic substitution of appropriately substituted precursors. Use of chiral organophosphorus compounds in some asymmetric transformations such as hydrogenation and alkyl/arylation reactions is also discussed.

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