Journal of Chemical Crystallography

, Volume 42, Issue 9, pp 911–915

Synthesis and Structure of 2-Cyclohexylamino-3-methyl-1,1-diphenyl-butan-1-ol (d-N-Cyclohexyl-diphenylvalinol), an Amino Alcohol Ligand Useful in Asymmetric Catalysis

  • Eric W. Reinheimer
  • A. J. Hickman
  • J. E. Moretti
  • X. Ouyang
  • Katherine A. Kantardjieff
  • Adam R. Johnson
Original Paper
  • 117 Downloads

Abstract

Amino alcohols are important ligands for the asymmetric catalytic hydroamination of aminoallenes to form chiral pyrrolidines. The amino alcohol d-N-cyclohexyl-diphenylvalinol was synthesized and crystallized by slow evaporation from a 7:1 ether:ethanol mixture. The molecule crystallizes in the monoclinic space group P21 with unit cell parameters a = 8.0724(8) Å, b = 14.4327(14) Å, c = 8.6752(9) Å and β = 107.098(2)° and contains one molecule in the asymmetric unit with all constituent atoms being on general positions. Close inspection of the solid-state structure revealed a strong intramolecular hydrogen bond between the hydrogen atom of the hydroxyl group and the amine nitrogen.

Graphical Abstract

Herein we report the solid state structure of the chiral amino alcohol D-N-cyclohexyl-diphenylvalinol, a molecule which can serve as a ligand for transition metal complexes that function as asymmetric hydroamination catalysts
.

Keywords

Hydroamination Asymmetric catalysis Chirality 

References

  1. 1.
    Hoover JM, Petersen JR, Pikul JH, Johnson AR (2004) Organometallics 23:4614CrossRefGoogle Scholar
  2. 2.
    Müller TE, Beller M (1998) Chem Rev 98:675CrossRefGoogle Scholar
  3. 3.
    Müller TE, Hultzsch KC, Yus M, Foubelo F, Tada M (2008) Chem Rev 108:3795CrossRefGoogle Scholar
  4. 4.
    Pohlki F, Doye S (2003) Chem Soc Rev 32:104CrossRefGoogle Scholar
  5. 5.
    Hultzsch KC (2005) Adv Synth Catal 347:367CrossRefGoogle Scholar
  6. 6.
    Hultzsch KC (2005) Org Biomol Chem 3:1819CrossRefGoogle Scholar
  7. 7.
    Doye S (2004) Synlett 10:1653CrossRefGoogle Scholar
  8. 8.
    Seayad J, Tillack A, Hartung CG, Beller M (2002) Adv Synth Catal 344:795CrossRefGoogle Scholar
  9. 9.
    Arredondo V, McDonald FE, Marks TJ (1999) Organometallics 18:1949CrossRefGoogle Scholar
  10. 10.
    Arseniyadis S, Gore J (1983) Tetrahedron Lett 24:3997CrossRefGoogle Scholar
  11. 11.
    Kinsman R, Lathbury D, Vernon P, Gallagher T (1987) J Chem Soc Chem Comm 243Google Scholar
  12. 12.
    Fox DNA, Gallagher T (1990) Tetrahedron 46:4697CrossRefGoogle Scholar
  13. 13.
    Meguro M, Yamamoto Y (1998) Tetrahedron Lett 39:5421CrossRefGoogle Scholar
  14. 14.
    Ackermann L, Bergman RG (2002) Org Lett 4:1475CrossRefGoogle Scholar
  15. 15.
    Ackermann L, Bergman RG (2003) J Am Chem Soc 125:11956CrossRefGoogle Scholar
  16. 16.
    Arredondo V, McDonald FE, Marks TJ (1998) J Am Chem Soc 120:4871CrossRefGoogle Scholar
  17. 17.
    Arredondo V, Tian S, McDonald FE, Marks TJ (1999) J Am Chem Soc 121:3633CrossRefGoogle Scholar
  18. 18.
    Morita N, Krause N. (2006) Eur J Org Chem 4634Google Scholar
  19. 19.
    LaLonde RL, Sherry BD, Kang EJ, Toste FD (2007) J Am Chem Soc 129:14148CrossRefGoogle Scholar
  20. 20.
    Petersen JR, Hoover JM, Kassel WS, Rheingold AL, Johnson AR (2005) Inorg Chim Acta 358:687CrossRefGoogle Scholar
  21. 21.
    Johnson JS, Bergman RG (2001) J Am Chem Soc 123:2923CrossRefGoogle Scholar
  22. 22.
    Hickman AJ, Hughs LD, Jones CM, Li H, Redford JE, Sobelman SJ, Kouzelos JA, Johnson AR (2009) Tetrahedron Asymmetr 20:1279CrossRefGoogle Scholar
  23. 23.
    Near KE, Chapin BM, McAnnally-Linz DC, Johnson AR (2011) J Organomet Chem 696:81CrossRefGoogle Scholar
  24. 24.
    Anderson LL, Arnold J, Bergman RG (2004) Org Lett 6:2519CrossRefGoogle Scholar
  25. 25.
    Lorber C, Choukroun R, Vendier L (2004) Organometallics 23:1845CrossRefGoogle Scholar
  26. 26.
    Herzon SB, Hartwig JF (2008) J Am Chem Soc 130:14940CrossRefGoogle Scholar
  27. 27.
    Herzon SB, Hartwig JF (2007) J Am Chem Soc 129:6690CrossRefGoogle Scholar
  28. 28.
    Eisenberger P, Ayinla RO, Lauzon J-MP, Schafer LL (2009) Angew Chem Int Ed 48:8680CrossRefGoogle Scholar
  29. 29.
    Hansen MC, Heusser CA, Narayan TC, Fong KE, Hara N, Kohn AW, Venning AR, Rheingold AL, Johnson AR (2011) Organometallics 30:4616CrossRefGoogle Scholar
  30. 30.
    SMART (1998) Software for the CCD detector system, version 5.050 (NT). Bruker Analytical X-ray Systems, MadisonGoogle Scholar
  31. 31.
    SAINT (1998) Software for the CCD detector system, version 5.01 (NT). Bruker Analytical X-ray Systems, MadisonGoogle Scholar
  32. 32.
    Blessing RH (1995) SADABS, program for absorption corrections using siemens CCD based on the method of Robert blessing. Acta Cryst A51:33Google Scholar
  33. 33.
    Sheldrick GM (1996) XPREP, program for space group determination. University of Göttingen, GöttingenGoogle Scholar
  34. 34.
    Speck AL (2001) PLATON, a multipurpose crystallographic tool. Utrecht University, UtrechtGoogle Scholar
  35. 35.
    Sheldrick GM (1997) SHELXS-97, program for crystal structure determination. University of Göttingen, GöttingenGoogle Scholar
  36. 36.
    Sheldrick GM (1997) SHELXL-97, program for the crystal structure refinement. University of Göttingen, GöttingenGoogle Scholar
  37. 37.
    Barbour LJ (2001) J Supramol Chem 1:189CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2012

Authors and Affiliations

  • Eric W. Reinheimer
    • 1
    • 4
  • A. J. Hickman
    • 2
  • J. E. Moretti
    • 2
  • X. Ouyang
    • 3
  • Katherine A. Kantardjieff
    • 1
    • 4
  • Adam R. Johnson
    • 2
  1. 1.Department of Chemistry, The W.M. Keck Foundation Center for Molecular StructureCalifornia State Polytechnic UniversityPomonaUSA
  2. 2.Department of ChemistryHarvey Mudd CollegeClaremontUSA
  3. 3.Department of Chemistry and Biochemistry, The W.M. Keck Foundation Center for Molecular StructureCalifornia State UniversityFullertonUSA
  4. 4.Department of Chemistry and Biochemistry, The W.M. Keck Foundation Center for Molecular StructureCalifornia State UniversitySan MarcosUSA

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