Direct Catalytic Synthesis of C(Sp2)–C(Sp3) Atropisomers with Simultaneous Control of Central and Axial Chirality

Chapter
Part of the Springer Theses book series (Springer Theses)

Abstract

In the previous chapter, we discussed about the synthesis of axially chiral compounds using an indirect method to generate a stereogenic axis. The key point was to break the symmetry of a molecule and “reveal” the blocked rotation of a single sp2–sp2 bond.

References

  1. 1.
    Di Iorio N, Filippini G, Mazzanti A, Righi P, Bencivenni G (2017) Controlling the C(sp3)–C(sp2) axial conformation in the enantioselective Friedel-Crafts-type alkylation of β-Naphthols with inden-1-ones. Org Lett 19(24):6692–6695.  https://doi.org/10.1021/acs.orglett.7b03415CrossRefGoogle Scholar
  2. 2.
    Gustafson JL, Lim D, Miller SJ (2010) Science, 1251CrossRefGoogle Scholar
  3. 3.
    Link A, Sparr C (2014) Angew Chem Int Ed, 5458Google Scholar
  4. 4.
    Staniland S, Adams RW, Grainger JJW, Turner NJ, Clayden J (2016) Angew Chem Int Ed, 10755Google Scholar
  5. 5.
    Joliffe JD, Armstrong RJ, Smith MD (2017) Nat Chem.  https://doi.org/10.1038/nchem.2710. (article in press)
  6. 6.
    Narute S, Parnes R, Toste DF, Pappo D (2016) J Am Chem Soc, 16533Google Scholar
  7. 7.
    Li GQ, Gao H, Keene G, Devonas M, Ess DH, Kurti L (2013) J Am Chem Soc, 7414Google Scholar
  8. 8.
    Chen YH, Cheng DJ, Zhang J, Wang Y, Liu XY, Tan B (2015) J Am Chem Soc, 15062Google Scholar
  9. 9.
    Zhang H–H, Wang C–S, Li C, Mei G–J, Li Y, Shi F (2016) Angew Chem Int Ed, 116Google Scholar
  10. 10.
    Moliterno M, Cari R, Puglisi A, Antenucci A, Sperandio C, Moretti E, Di Sabato A, Salvio R, Bella M (2016) Angew Chem Int Ed, 6525Google Scholar
  11. 11.
    Brandes S, Bella M, Kjoersgaard A, Jørgensen KA (2006) Angew Chem Int Ed, 1147Google Scholar
  12. 12.
    Lomas JS, Dubois J–E (1976) J Org Chem, 3033Google Scholar
  13. 13.
    Lomas JS, Luong PK, Dubois J–E (1977) J Org Chem, 3394Google Scholar
  14. 14.
    Lomas JS, Anderson JE (1995) J Org Chem, 3246Google Scholar
  15. 15.
    Wolf C, Pranatharthiharan L,. Ramagosa RB (2002) Tetrahedron Lett, 8563Google Scholar
  16. 16.
    Casarini D, Lunazzi L, Mazzanti A (1997) J Org Chem, 3315Google Scholar
  17. 17.
    Ford TW, Thompson TB, Snoble KAJ, Timko JM (1975) J Am Chem Soc, 95Google Scholar
  18. 18.
    Paradisi PR, Mazzanti A, Ranieri S, Bencivenni G (2012) Chem Commun, 11178Google Scholar
  19. 19.
    Still WC, Kahn M, Mitra AJ (1978) J Org Chem 43:2923CrossRefGoogle 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

Personalised recommendations