Journal of the American Chemical Society
Communication
P.; De Zotti, M.; Peggion, C.; Formaggio, F.; Toniolo, C. J. Am. Chem.
Soc. 2008, 130, 5986.
(8) (a) Sciebura, J.; Skowronek, P.; Gawronski, J. Angew. Chem., Int. Ed.
2009, 48, 7069. (b) Sciebura, J.; Gawronski, J. Chem.Eur. J. 2011, 17,
13138.
sufficient for HTS applications. We also observed that a red shift
in the UV spectrum occurs upon substrate recognition which has
potential for analysis of the total analyte concentration.
In conclusion, we have introduced a universal probe 2 that can
be used for chirality sensing of many monoamines, diamines,
amino alcohols, amino acids, and α-hydroxy acids. The
enantioselective chemosensing is based on asymmetric trans-
formation of the first kind of stereolabile zinc and boron
binaphtholates that undergo prompt chiral amplification upon
coordination of a chiral substrate. The central-to-axial chirality
induction process can easily be measured by CD spectroscopy,
and the sign and the amplitude of the Cotton effect can be
correlated to the absolute configuration and ee of the samples
tested.
(9) (a) Ghosn, M. W.; Wolf, C. J. Am. Chem. Soc. 2009, 131, 16360.
(b) Ghosn, M. W.; Wolf, C. J. Org. Chem. 2011, 76, 3888. (c) Ghosn, M.
W.; Wolf, C. Tetrahedron 2011, 67, 6799. (d) Iwaniuk, D. P.; Wolf, C. J.
Am. Chem. Soc. 2011, 133, 2414. (e) Iwaniuk, D. P.; Wolf, C. Org. Lett.
2011, 13, 2602. (f) Iwaniuk, D. P.; Bentley, K. W.; Wolf, C. Chirality
2012, 24, 584. (g) Iwaniuk, D. P.; Wolf, C. Chem. Commun. 2012, 48,
11226. (h) Zhang, P.; Wolf, C. Chem. Commun. 2013, 49, 7010.
(i) Bentley, K. W.; Wolf, C. J. Am. Chem. Soc. 2013, 135, 12200.
(10) (a) Kim, H.; So, S. M.; Yen, C. P.-H.; Vinhato, E.; Lough, A. J.;
Hong, J.-I.; Kim, H.-J.; Chin, J. Angew. Chem., Int. Ed. 2008, 47, 8657.
(b) Waki, M.; Abe, H.; Inouye, M. Angew. Chem., Int. Ed. 2007, 46, 3059.
(c) Katoono, R.; Kawai, H.; Fujiwara, K.; Suzuki, T. J. Am. Chem. Soc.
2009, 131, 16896. (d) Wezenberg, S. J.; Salassa, G.; Escudero-Adan, E.
C.; Benet-Buchholz, J.; Kleij, A. W. Angew. Chem., Int. Ed. 2011, 50, 713.
(e) Wolf, C.; Bentley, K. W. Chem. Soc. Rev. 2013, 42, 5408.
(11) (a) Eelkema, R.; Feringa, B. L. J. Am. Chem. Soc. 2005, 127, 13480.
(b) Mizutani, T.; Tagaki, H.; Hara, O.; Horiguchi, T.; Ogoshi, H.
Tetrahedron Lett. 1997, 38, 1991. (c) Ishii, Y.; Onda, Y.; Kubo, Y.
Tetrahedron Lett. 2006, 47, 8221. (d) Etxebarria, J.; Degenbeck, H.;
Felten, A.-S.; Serres, S.; Nieto, N.; Vidal-Ferran, A. J. Org. Chem. 2009,
74, 8794.
(12) (a) Reetz, M. T.; Neugebauer, T. Angew. Chem., Int. Ed. 1999, 38,
179. (b) Mikami, K.; Terada, M.; Korenaga, T.; Matsumoto, Y.; Ueki,
M.; Angelaud, R. Angew. Chem., Int. Ed. 2000, 39, 3532. (c) Walsh, P.;
Lurain, A.; Balsells, J. Chem. Rev. 2003, 103, 3297. (d) Reetz, M. T.; Li, X.
Angew. Chem., Int. Ed. 2005, 44, 2959. (e) Aikawa, K.; Kojima, M.;
Mikami, K. Angew. Chem., Int. Ed. 2009, 48, 6073. (f) Aikawa, K.;
Mikami, K. Chem. Commun. 2012, 48, 11050.
(13) (a) Mikami, K.; Matuskawa, S. Nature 1997, 385, 613. (b) Gajewy,
J.; Gawronski, J.; Kwit, M. Monatsh. Chem. 2012, 143, 1045. (c) Ueki,
M.; Matsumoto, Y.; Jodry, J.; Mikami, K. Synlett 2001, 1889.
ASSOCIATED CONTENT
* Supporting Information
■
S
Synthetic details, analytical procedures, MS, UV, CD,
fluorescence and NMR spectra, and X-ray analysis. This material
AUTHOR INFORMATION
Corresponding Author
■
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
This material is based upon work supported by the NSF under
CHE-1213019. We gratefully acknowledge additional NSF
support for J.M.M. (REU-1156788).
́
(d) Chavarot, M.; Byrne, J.; Chavant, P.; Pardillos-Guindet, J.; Vallee,
REFERENCES
■
Y. Tetrahedron: Asymmetry 1998, 9, 3889. (e) Bolm, C.; Beckmann, O.
Chirality 2000, 12, 523. (f) Gajewy, J.; Gawronski, J.; Kwit, M. Eur. J.
Org. Chem. 2013, 307.
(1) Leung, D.; Kang, S. O.; Anslyn, E. V. Chem. Soc. Rev. 2012, 41, 448.
(2) (a) Matile, S.; Berova, N.; Nakanishi, K.; Novkova, S.; Philpova, I.;
Blagoev, B. J. Am. Chem. Soc. 1993, 33, 2072. (b) Huang, X.; Fujioka, N.;
Pescitelli, G.; Koehn, F. E.; Williamson, R. T.; Nakanishi, K.; Berova, N.
J. Am. Chem. Soc. 2002, 124, 10320. (c) Balaz, M.; De Napoli, M.;
Holmes, A. E.; Mammana, A.; Nakanishi, K.; Berova, N.; Purrello, R.
Angew. Chem., Int. Ed. 2005, 44, 4006. (d) Berova, N.; Pescitelli, G.;
Petrovic, A. G.; Proni, G. Chem. Commun. 2009, 5958.
(3) (a) Superchi, S.; Casarini, D.; Laurita, A.; Bavoso, A.; Rosini, C.
Angew. Chem., Int. Ed. 2001, 40, 451. (b) Superchi, S.; Bisaccia, R.;
Casarini, D.; Laurita, A.; Rosini, C. J. Am. Chem. Soc. 2006, 128, 6893.
(c) Tartaglia, S.; Padula, D.; Scafato, P.; Chiummiento, L.; Rosini, C. J.
Org. Chem. 2008, 73, 4865.
(4) (a) Nieto, S.; Lynch, V.; Anslyn, E.; Kim, H.; Chin, J. J. Am. Chem.
Soc. 2008, 130, 9232. (b) Nieto, S.; Dragna, J.; Anslyn, E. Chem.Eur. J.
2010, 16, 227. (c) Leung, D.; Anslyn, E. Org. Lett. 2011, 13, 2298.
(d) Joyce, L. A.; Maynor, M. S.; Dragna, J. M.; da Cruz, G. M.; Lynch, V.
M.; Canary, J. W.; Anslyn, E. V. J. Am. Chem. Soc. 2011, 133, 13746.
(e) You, L.; Berman, J. S.; Anslyn, E. V. Nat. Chem. 2011, 3, 943. (f) You,
L.; Pescitelli, G.; Anslyn, E. V.; Di Bari, L. J. Am. Chem. Soc. 2012, 134,
7117. (g) Joyce, L.; Canary, J.; Anslyn, E. Chem.Eur. J. 2012, 18, 8064.
(5) (a) Holmes, A.; Zahn, S.; Canary, J. Chirality 2002, 14, 471.
(b) Holmes, A. E.; Das, D.; Canary, J. W. J. Am. Chem. Soc. 2007, 129,
1506.
(14) (a) Maier, F.; Trapp, O. Angew. Chem., Int. Ed. 2012, 51, 2985.
(b) Wolf, C. Chem. Soc. Rev. 2005, 34, 595.
(15) Tudor, M. D.; Becker, J. J.; White, P. S.; Gagne,
́
M. R.
Organometallics 2000, 19, 4376.
(16) Desponds, O.; Schlosser, M. Tetrahedron Lett. 1996, 37, 47.
(17) Sahnoun, R.; Koseki, S.; Fujimura, Y. J. Phys. Chem. A 2006, 110,
2440.
(18) Wolf, C., Ed. Dynamic Stereochemistry of Chiral Compounds; RSC
Publishing: Cambridge, 2008; p 86.
(19) 2,2′-Binaphthalene-1,1′-diol, 2, is the stereodynamic analogue of
BINOL (1,1′-binaphthalene-2,2′-diol).
(20) Costa, A. M.; Jimeno, C.; Gavenonis, J.; Carrol, P.; Walsh, P. J. Am.
Chem. Soc. 2002, 124, 6929.
(21) (a) Shan, Z. X.; Liu, S. M.; Liu, D. J. Chin. J. Chem. 2003, 21, 1373.
́
(b) Freire, F.; Quinoa, E.; Riguera, R. Chem. Commun. 2008, 4147.
̃
(22) Chiral boron receptors: (a) Zhao, J.; Fyles, T. M.; James, T. D.
Angew. Chem., Int. Ed. 2004, 43, 3461. (b) Zhu, L.; Zhong, Z.; Anslyn, E.
V. J. Am. Chem. Soc. 2005, 127, 4260. (c) Shabbir, S. H.; Regan, C. J.;
Anslyn, E. V. Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 10487. (d) Mirri, G.;
Bull, S. D.; Horton, P. N.; James, T. D.; Male, L.; Tucker, J. H. R. J. Am.
Chem. Soc. 2010, 132, 8903. (e) Bull, S. T.; Davidson, M. G.; van den
Elsen, J. M. H.; Fossey, J. S.; Jenkins, A. T. A.; Jiang, Y.-B.; Kubo, Y.;
Marken, F.; Sakurai, K.; Zhao, J.; James, T. D. Acc. Chem. Res. 2012, 46,
312.
(6) (a) Li, X.; Tanasova, M.; Vasileiou, C.; Borhan, B. J. Am. Chem. Soc.
2008, 130, 1885. (b) Li, X.; Borhan, B. J. Am. Chem. Soc. 2008, 130,
16126. (c) Li, X.; Burrell, C. E.; Staples, R. J.; Borhan, B. J. Am. Chem.
Soc. 2012, 134, 9026.
(7) (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.
(b) Dutot, L.; Wright, K.; Gaucher, A.; Wakselman, M.; Mazaleyrat, J.-
(23) Metola, P.; Anslyn, E. V.; James, T. D.; Bull, S. D. Chem. Sci. 2012,
3, 156.
(24) Nonlinear effects in catalysis and chromatography: (a) Satyanar-
ayana, T.; Abraham, S.; Kagan, H. B. Angew. Chem., Int. Ed. 2009, 48,
456. (b) Trapp, O.; Schurig, V. Tetrahedron: Asymmetry 2010, 21, 1334.
18055
dx.doi.org/10.1021/ja410428b | J. Am. Chem. Soc. 2013, 135, 18052−18055