Chiral amplification with a stereodynamic triaryl probe: Assignment of the absolute configuration and enantiomeric excess of amino alcohols

Journal of the American Chemical Society

Volumn 131, Issue 45, 2009, Pages 16360-16361

  Ghosn, Marwan W ^a   Wolf, Christian ^a  

^a GEORGETOWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE CONFIGURATION; AMINO ALCOHOLS; CHIRAL AMPLIFICATION; COTTON EFFECTS; DIIMINES; ENANTIOMERIC EXCESS; IN-SITU;

ALCOHOLS; AMINATION; AMPLIFICATION; ONTOLOGY; PROBES;

AMINES;

ALCOHOL; AMINE; AMINO ACID; CARBOXYLIC ACID;

ARTICLE; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; CONFORMATION; ENANTIOMER;

AMINO ALCOHOLS; CIRCULAR DICHROISM; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; NAPHTHALENES; PHENOLS; STEREOISOMERISM;

EID: 70450169432     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja907741v     Document Type: Article

References (36)

1. Nieto, S.; Lynch, V. M.; Anslyn, E. V.; Kim, H.; Chin, J. J. Am. Chem. Soc. 2008, 130, 9232.
2. (a) Bobek, M. M.; Krois, D.; Brinker, U. H. Org. Lett. 2000, 2, 1999.
3. (b) Bakirci, H.; Zhang, X.; Nau, W. M. J. Org. Chem. 2005, 70, 39.
4. Owen, D. J.; VanDerveer, D.; Schuster, G. B. J. Am. Chem. Soc. 1998, 120, 1705.
5. Das, N.; Ghosh, A.; Singh, O. M.; Stang, P. J. Org. Lett. 2006, 8, 1701.
6. (a) Gawronski, J.; Kazmierczak, F.; Gawronska, K.; Rychlewska, U.; Norden, B.; Holmen, A. J. Am. Chem. Soc. 1998, 120, 12083.
7. (b) Kobayashi, N.; Higashi, R.; Titeca, B. C.; Lamote, F.; Ceulemans, A. J. Am. Chem. Soc. 1999, 121, 12018.
8. (c) Hosoi, S.; Kamiya, M.; Ohta, T. Org. Lett. 2001, 3, 3659.
9. (a) Gawronski, J.; Grajewski, J. Org. Lett. 2003, 5, 3301.
10. (b) Berova, N.; Di Bari, L.; Pescitelli, G. Chem. Soc. Rev. 2007, 36, 914.
11. (a) Mazaleyrat, J.-P.; Wright, K.; Gaucher, A.; Toulemonde, N.; Wakselman, M.; Oancea, S.; Peggion, C.; Formaggio, F.; Setnicka, V.; Keiderling, T. A.; Toniolo, C. J. Am. Chem. Soc. 2004, 126, 12874.
12. (b) Superchi, S.; Bisaccia, R.; Casarini, D.; Laurita, A.; Rosini, C. J. Am. Chem. Soc. 2006, 128, 6893.
13. (c) Dutot, L.; Wright, K.; Gaucher, Wakselman, M.; Mazaleyrat, J.-P.; De Zotti, M.; Peggion, C.; Formaggio, F.; Toniolo, C. J. Am. Chem. Soc. 2008, 130, 5986.
14. Waki, M.; Abe, H.; Inouye, M. Angew. Chem., Int. Ed. 2007, 46, 3059.
15. Selected examples: (a) Borovkov, V. V.; Lintuluoto, J. M.; Inoue, Y. J. Am. Chem. Soc. 2001, 123, 2979.
16. (b) Proni, G.; Pescitelli, G.; Huang, X.; Nakanishi, K.; Berova, N. J. Am. Chem. Soc. 2003, 125, 12914.
17. (c) Huang, X.; Fujioka, N.; Pescitelli, G.; Koehn, F. E.; Williamson, R. T.; Nakanishi, K.; Berova, N. J. Am. Chem. Soc. 2002, 124, 10320.
18. (d) Holmes, A. E.; Das, D.; Canary, J. W. J. Am. Chem. Soc. 2007, 129, 1506.
19. (a) Zahn, S.; Canary, J. W. Org. Lett. 1999, 1, 861.
20. (b) Tsukube, H.; Hosokubo, M.; Wada, M.; Shinoda, S.; Tamiaki, H. Inorg. Chem. 2001, 40, 740.
21. (c) Eelkema, R.; Feringa, B. L. J. Am. Chem. Soc. 2005, 127, 13480.
22. (a) Wolf, C.; Tumambac, G. E. J. Phys. Chem. A. 2003, 107, 815.
23. (b) Tumambac, G. E.; Wolf, C. J. Org. Chem. 2004, 69, 2048.
24. (c) Tumambac, G. E.; Wolf, C. J. Org. Chem. 2005, 70, 2930.
25. (a) Mei, X.; Wolf, C. Chem. Commun. 2004, 2078.
26. (b) Mei, X.; Wolf, C. J. Am. Chem. Soc. 2004, 126, 14736.
27. (c) Tumambac, G. E.; Wolf, C. Org. Lett. 2005, 7, 4045.
28. (d) Mei, X.; Martin, R. M.; Wolf, C. J. Org. Chem. 2006, 71, 2854.
29. (e) Liu, S.; Pestano, J. P. C.; Wolf, C. J. Org. Chem. 2008, 73, 4267.
30. (f) Mei, X.; Wolf, C. J. Am. Chem. Soc. 2006, 128, 13326.
31. Watkinson, M.; Whiting, A.; McAuliffe, C. A. J. Chem. Soc., Chem. Commun. 1994, 2141.
32. Wolf, C., Ed. Dynamic Stereochemistry of Chiral Compounds; RSC: Cambridge, 2008.
33. NMR and MS reaction monitoring did not show any sign of the monoimine indicating that the second condensation step is faster than the first.
34. Smith, H. E. Chem. Rev. 1998, 98, 1709.
35. The amino diols 10 and 11 show weak CD signals, probably due to competitive hydrogen bonding of the two available hydroxyl groups.
36. Salicylidenimines can form a CD active quinoid-like tautomer. The ICD observed with 1 is more likely a result of ECCD. NMR and X-ray analysis do not show the quinoid structure. The phenolic C-O bond lengths in 13 and 14 are 1.357 and 1.361 Å, which is close to the value in phenol (1.349 Å); the C-O bond length in quinone is 1.294 Å. Ligtenbarg, A. G. J.; Hage, R.; Meetsma, A.; Feringa, B. L. J. Chem. Soc., Perkin Trans. 2 1999, 807.