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Targeting the Remote Control of Axial Chirality in N-(2-tert-butylphenyl)Succinimides via a Desymmetrization Strategy

  • Nicola Di Iorio
Chapter
Part of the Springer Theses book series (Springer Theses)

Abstract

There are molecules possessing stereogenic elements that are not chiral. These compounds are termed “meso” and do not manifest chirality because they possess a symmetry element of the second order (i.e. a symmetry plane)2 that makes their mirror images superimposable (Fig. 3.1).
Fig. 3.1

Meso form of tartaric acid

References

  1. 1.
    Di Iorio N, Righi P, Mazzanti A, Mancinelli M, Ciogli A, Bencivenni G (2014) J Am Chem Soc 10:250Google Scholar
  2. 2.
    Di Iorio N, Champavert F, Erice A, Righi P, Mazzanti A, Bencivenni G (2016) Tetrahedron (invited paper) 5191 (special issue “Methods for controlling axial chirality”)Google Scholar
  3. 3.
    Di Iorio N, Soprani L, Crotti S, Marotta E, Mazzanti A, Righi P, Bencivenni G (2017) Synthesis (invited paper) 1519Google Scholar
  4. 4.
    IUPAC (1997) Compendium of chemical terminology, 2nd ed. (the “Gold Book”). OxfordGoogle Scholar
  5. 5.
    Zeng XP, Cao ZY, Wang YH, Zhou F, Zhou J (2016) Chem Rev 7330Google Scholar
  6. 6.
    Borissov A, Davies TQ, Ellis SR, Fleming TA, Richardson MSW, Dixon DJ (2016) Chem Soc Rev 5474Google Scholar
  7. 7.
    Yamagata ADG, Datta S, Jackson KE, Stegbauer L, Paton RS, Dixon DJ (2015) Angew Chem Int Ed 4899Google Scholar
  8. 8.
    Curran DP, Qi H, Geib SJ, DeMello NC (1994) J Am Chem Soc 3131Google Scholar
  9. 9.
    Bencivenni G, Galzerano P, Mazzanti A, Bartoli G, Melchiorre P (2010) Proc Natl Acad Sci 20:642Google Scholar
  10. 10.
    Still WC, Kahn M, Mitra AJ (1978) J Org Chem 43:2923CrossRefGoogle Scholar
  11. 11.
    Cassani C, Rapun RM, Arceo E, Bravo F, Melchiorre P (2013) Nat Protoc 325Google Scholar
  12. 12.
    Krafft ME, Wright JA (2006) Chem Commun 2977–2979Google Scholar
  13. 13.
    Wamg X, Reisinger CM (2008) B List J Am Chem Soc 130:6070–6071CrossRefGoogle Scholar
  14. 14.
    Nolwenn JAM (2006) B List J Am Chem Soc 128:13368–13369CrossRefGoogle Scholar
  15. 15.
    Bergman R, Magnusson G (1986) J Org Chem 51:212–217CrossRefGoogle Scholar
  16. 16.
    Hadjiarapoglou L, Klein I, Spitzner D, de Meijere A (1996) Synthesis 525–528Google Scholar
  17. 17.
    Neumann JJ, Rakshit S, Dröge T, Glorius F (2009) Angew Chem Int Ed 48:6892–6895CrossRefGoogle Scholar
  18. 18.
    Miller C, Hoyle C, Jönsson E (1998) PCT WO 98/54:134Google Scholar
  19. 19.
    Hamashima Y, Suzuki T, Takano H, Shimura Y, Sodeoka M (2005) J Am Chem Soc 10:164Google Scholar
  20. 20.
    Zhu XL, Xu JH, Cheng DJ, Zhao LJ, Liu XY, Tan B (2014) Org Lett 2192Google Scholar

Copyright information

© Springer International Publishing AG, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of Industrial Chemistry “Toso Montanari”University of BolognaBolognaItaly

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