Synthesis of a protonated C2-symmetric N,N-chiral 'proton sponge'

Tetrahedron Letters

Volumn 39, Issue 26, 1998, Pages 4733-4736

  Charmant, Jonathan P H ^a   Lloyd Jones, Guy C ^a   Peakman, Torren M ^a   Woodward, Robert L ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

NAPHTHALENE DERIVATIVE;

ARTICLE; CHIRALITY; DIASTEREOISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; REACTION ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0032565849     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00930-7     Document Type: Article

References (18)

1. 1. R. W. Alder, Chem. Rev., 1989, 89, 1215-1223.
2. 2. The unusual basicity of 2 was first reported by Alder et al: R. W. Alder, P. S. Bowman, W. R. S. Steele, D. R. Winterman, J. Chem. Soc., Chem. Commun., 1968, 723-724.
3. 3. Review: H. A. Staab, T. Saupe, Angew. Chem. Int. Ed. Engl., 1988, 27, 865-879.
4. 4. R. W. Alder, N. C. Goode, N. Miller, F. Hibbert, K. P. P. Hunte, H. J. Robbins, J. Chem. Soc., Chem. Commun., 1978, 89-90.
5. 5. F. Hibbert, S. Phillips, J. Chem. Research (S), 1990, 90-91 and references therein.
6. 6. H. A. Staab, C. Krieger, G. Hieber, K. Oberdorf, Angew. Chem., Int. Ed. Engl., 1997, 36, 1884-1886.
7. 7. J. M. Lehn, Fortschritte der Chemischen Forschung, 1970, 15, 311.
8. 2V transition state (or midpoint) has been proposed for 1 (non-automerisation) - R. W. Alder, J. E. Anderson, J. Chem. Soc., Perkin Trans. 2, 1973, 2086-2088.
9. + see: J. A. Gerlt, M. M. Kreevoy, W. W Cleland, P. A. Frey, Chemistry & Biology, 1997, 4, 259-267; J. P. Guthrie, idem, 1996, 3, 163-170; G. H. Barnett, F. Hibbert, J. Am. Chem. Soc., 1984, 106, 2080; For leading references on asymmetric H-bonds, see: C. L. Perrin, J. B. Nielson, J. Am. Chem. Soc., 1997, 119, 12734-12741.
10. + see: J. A. Gerlt, M. M. Kreevoy, W. W Cleland, P. A. Frey, Chemistry & Biology, 1997, 4, 259-267; J. P. Guthrie, idem, 1996, 3, 163-170; G. H. Barnett, F. Hibbert, J. Am. Chem. Soc., 1984, 106, 2080; For leading references on asymmetric H-bonds, see: C. L. Perrin, J. B. Nielson, J. Am. Chem. Soc., 1997, 119, 12734-12741.
11. + see: J. A. Gerlt, M. M. Kreevoy, W. W Cleland, P. A. Frey, Chemistry & Biology, 1997, 4, 259-267; J. P. Guthrie, idem, 1996, 3, 163-170; G. H. Barnett, F. Hibbert, J. Am. Chem. Soc., 1984, 106, 2080; For leading references on asymmetric H-bonds, see: C. L. Perrin, J. B. Nielson, J. Am. Chem. Soc., 1997, 119, 12734-12741.
12. + see: J. A. Gerlt, M. M. Kreevoy, W. W Cleland, P. A. Frey, Chemistry & Biology, 1997, 4, 259-267; J. P. Guthrie, idem, 1996, 3, 163-170; G. H. Barnett, F. Hibbert, J. Am. Chem. Soc., 1984, 106, 2080; For leading references on asymmetric H-bonds, see: C. L. Perrin, J. B. Nielson, J. Am. Chem. Soc., 1997, 119, 12734-12741.
13. 10. G. Bar-Haim, R. Shach, M. Kol, Chem. Commun., 1997, 229-230; G. Bar-Haim, M. Kol, J. Org. Chem., 1997, 62, 6682-6683.
14. 10. G. Bar-Haim, R. Shach, M. Kol, Chem. Commun., 1997, 229-230; G. Bar-Haim, M. Kol, J. Org. Chem., 1997, 62, 6682-6683.
15. -1. Clearly, the N-H group acts as some form of stereochemical lock.
16. 13C-NMR, (HR)MS and elemental analysis. Full experimental details will be reported in due course.
17. 2 at 21 °C, reproducibly gave an 88.5 / 11.5 ratio of diastereomers.
18. 14 Benzyl iodide was prepared according to the method of Coleman and Hauser: (NaI, acetone, benzyl chloride, reflux 1 hr) and then recrystallised from ethanol five times (52 % yield overall). G. H. Coleman, C. R. Hauser. J. Am. Chem. Soc., 1928, 50, 1196