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LETTER
(6) (a) Organic Synthesis in Water; Lindström, U. M., Ed.;
10 and extracted with EtOAc (3 × 2 mL). The combined organic
layers were dried over anhyd Na2SO4, the solvent was evaporated,
and the crude product was charged on a Et3N pretreated silica gel
column chromatography [Et2O–PE (1:1); silica/sample = 30:1].
Pure 1-phenoxy-3-(2¢-fluorophenylamino)propan-2-ol (3fe) was
isolated as a colorless oil (91% yield).
Blackwell: Oxford, 2007. (b) Li, C.-J. Chem. Rev. 2005,
105, 3095. (c) Lindström, U. M. Chem. Rev. 2002, 102,
2751. (d) Manabe, K.; Kobayashi, S. Chem. Eur. J. 2002, 8,
4095. (e) Fringuelli, F.; Piermatti, O.; Pizzo, F.; Vaccaro, L.
Eur. J. Org. Chem. 2001, 439. (f) Organic Synthesis in
Water; Grieco, P. A., Ed.; Blackie Academic and
Professional: London, 1998. (g) Li, C. J.; Chang, T. H. In
Organic Reactions in Aqueous Media; Wiley: New York,
1997.
Physical Data for 3fe
1H NMR (CDCl3): d = 2.80–3.70 (br s, 2 H), 3.34 (dd, 1 H, J = 6.9,
12.9 Hz), 3.47 (dd, 1 H, J = 3.9, 13.0 Hz), 4.00–4.15 (m, 2 H), 4.20–
4.35 (m, 1 H), 6.60–6.70 (m, 1 H), 6.77 (t, 1 H, J = 8.2 Hz), 6.90–
7.05 (m 5 H), 7.20–7.35 (m 2 H). 13C NMR (CDCl3): d = 158.3,
151.9, 136.3, 129.6, 124.6, 121.4, 117.5, 114.7, 114.5, 112.6, 69.9,
68.7, 46.4. 19F NMR (CDCl3): d = –136.3 (m). Anal. Calcd for
C15H16FNO2: C, 68.95; H, 6.17; F, 7.27; N, 5.36. Found: C, 68.81;
H, 5.92; F, 7.02; N, 5.44. GC-MS (EI): m/z (%) = 261 (13) [M+], 124
(100), 77 (30).
(7) Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem. Int.
Ed. 2001, 40, 2004.
(8) (a) Fringuelli, F.; Pizzo, F.; Tortoioli, S.; Vaccaro, L. Org.
Lett. 2005, 7, 4411. (b) Fringuelli, F.; Pizzo, F.; Vaccaro, L.
J. Org. Chem. 2004, 69, 2315. (c) Fringuelli, F.; Pizzo, F.;
Tortoioli, S.; Vaccaro, L. Green Chem. 2003, 5, 436.
(d) Fringuelli, F.; Pizzo, F.; Tortoioli, S.; Vaccaro, L. J. Org.
Chem. 2003, 68, 8248. (e) Fringuelli, F.; Pizzo, F.; Rucci,
M.; Vaccaro, L. J. Org. Chem. 2003, 68, 7041.
Acknowledgment
(f) Fringuelli, F.; Pizzo, F.; Tortoioli, S.; Vaccaro, L. Adv.
Synth. Catal. 2002, 344, 379. (g) Fringuelli, F.; Pizzo, F.;
Vaccaro, L. J. Org. Chem. 2001, 66, 3554. (h) Fringuelli,
F.; Pizzo, F.; Vaccaro, L. J. Org. Chem. 2001, 66, 4719.
(i) Fringuelli, F.; Piermatti, O.; Pizzo, F.; Vaccaro, L. J. Org.
Chem. 1999, 64, 6094.
The Ministero dell’Istruzione dell’Università e della Ricerca
(MIUR) and the Università degli studi di Perugia are thanked for
financial support (COFIN 2006: ‘Catalizzatori, metodologie e
processi innovativi per il regio- e stereocontrollo delle sintesi
organiche’).
(9) (a) Bonollo, S.; Fringuelli, F.; Pizzo, F.; Vaccaro, L. Green
Chem. 2006, 8, 960. (b) Wu, J.; Xia, H.-G. Green Chem.
2005, 7, 708. (c) Surendra, K.; Krishnaveni, N. S.; Rao, K.
R. Synlett 2005, 506. (d) Azizi, M.; Saidi, M. R. Org. Lett.
2005, 7, 3649.
References and Notes
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(11) As representative examples, see: (a) Boudou, M.; Ogawa,
C.; Kobayashi, S. Adv. Synth. Catal. 2006, 348, 2585.
(b) Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35,
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(d) Kobayashi, S.; Mori, Y.; Nagayama, W.; Manabe, K.
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(13) (a) Fioroni, G.; Fringuelli, F.; Pizzo, F.; Vaccaro, L. Green
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S.; Vaccaro, L. J. Org. Chem. 2003, 68, 8248.
(5) Literature examples in this field are countless; for some
recent examples, see: (a) Yarapathy, V. R.; Mekala, S.; Rao,
B. V.; Tammishetti, S. Catal. Commun. 2006, 7, 466.
(b) Williams, D. G. B.; Lawton, M. Tetrahedron Lett. 2006,
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(d) Placzek, A. T.; Donelson, J. L.; Trivedi, R.; Gibbs, R. A.;
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Q.; Xu, L.-W.; Xia, C.-G. Synlett 2004, 846. (f) Carree, F.;
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(g) Rodriquez, J. R.; Navarro, A. Tetrahedron Lett. 2004, 45,
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Tetrahedron Lett. 2004, 45, 8253. (i) Ollevier, T.; Lavie-
Compin, G. Tetrahedron Lett. 2004, 45, 49. (j)Chakraborti,
A. K.; Rudrawar, S.; Kondaskar, A. Org. Biomol. Chem.
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Tetrahedron Lett. 2003, 44, 8315.
(c) Amantini, D.; Fringuelli, F.; Pizzo, F.; Tortoioli, S.;
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(e) Amantini, D.; Fringuelli, F.; Pizzo, F.; Vaccaro, L. Green
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(g) Fringuelli, F.; Pizzo, F.; Vaccaro, L. Synlett 2000, 311.
(14) The pH value reported is that measured in the clear aqueous
layer completely separated from the organic one. A pH
meter equipped with a combined refillable pH electrode and
with an autocompensating temperature control (ATC) probe
was used.
Synlett 2007, No. 17, 2683–2686 © Thieme Stuttgart · New York