E. Papavassilopoulou et al. / Tetrahedron Letters 48 (2007) 8323–8325
8325
10. Shono, T.; Masuda, H.; Murase, H.; Shimomura, M.;
Kashimura, S. J. Org. Chem. 1992, 57, 1061–1063.
11. Soai, K.; Yokoyama, S.; Mochida, K. Synthesis 1987,
647–648.
12. Kokotos, G. Synthesis 1990, 299–301.
13. Rodriguez, M.; Llinaero, M.; Doulet, S.; Heitz, A.;
Martinez, J. Tetrahedron Lett. 1991, 32, 923–926.
14. Bandgar, B. P.; Modhave, R. K.; Wadgaonkar, P. P.;
Sande, A. R. J. Chem. Soc., Perkin Trans. 1 1996, 1993–
1994.
15. Fujisawa, T.; Mon, T.; Sato, T. Chem. Lett. 1983, 835–
838.
16. Nikawa, J.; Shiba, T. Chem. Lett. 1979, 981–982.
17. McGeary, R. P. Tetrahedron Lett. 1998, 39, 3319–3322.
18. Kokotos, G.; Noula, C. J. Org. Chem. 1996, 61, 6994–
6996.
obtained products in very short times, combined with
high optical purity in the case of 2-amino alcohols from
L-amino acids, are prominent features of the present
method.
General procedure: To a suspension of NaBH4 (1.2–
1.5 mmol)32 in dry THF (2–3 mL), pentafluorophenyl
ester (1 mmol) was added and the mixture was stirred
at room temperature. The reaction was followed by
TLC and upon completion, the mixture was cooled to
0 °C, acidified with 1 N HCl and evaporated under
vacuum. The residue was diluted with ethyl acetate
and washed with water and brine. After drying over
Na2SO4 and evaporation of the solvent, the product
was isolated and purified by recrystallization, column
chromatography or preparative TLC.
19. Falorni, M.; Porcheddu, A.; Taddei, M. Tetrahedron Lett.
1999, 40, 4395–4396.
20. Saeed, A.; Ashraf, Z. J. Chem. Sci. 2006, 118, 419–
423.
21. McKennon, M.; Meyers, A. I. J. Org. Chem. 1993, 58,
3568–3571.
Acknowledgement
Financial support from the Special Research Account of
the University of Athens is highly appreciated.
22. Naqvi, T.; Bhattacharya, M.; Haq, W. J. Chem. Res. (S)
1999, 424–425.
23. Periasamy, M.; Thirumalaikumar, M. J. Organomet.
Chem. 2000, 609, 137–153.
References and notes
24. Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149–
164.
25. (a) Kokotos, G.; Constantinou-Kokotou, V.; Fernandez,
E. O.; Toth, I.; Gibbons, W. A. Liebigs Ann. Chem. 1992,
961–964; (b) Kokotos, G.; Constantinou-Kokotou, V. J.
Chem. Res. (S) 1992, 391, 3117–3132.
26. Kokotos, G.; Markidis, T.; Constantinou-Kokotou, V.
Synthesis 1996, 1223–1226.
27. Chiou, A.; Markidis, T.; Constantinou-Kokotou, V.;
Verger, R.; Kokotos, G. Org. Lett. 2000, 2, 347–350.
28. Kokotos, G.; Constantinou-Kokotou, V.; Noula, C.;
Hadjipavlou-Litina, D. Lipids. 1999, 34, 307–311.
29. Markidis, T.; Padron, J. M.; Martin, V. S.; Peters, G. J.;
Kokotos, G. Anticancer Res. 2001, 21, 2835–2840.
30. Kovacs, J.; Kisfaludy, L.; Ceprini, M. Q. J. Am. Chem.
Soc. 1967, 89, 183–184.
1. Larock, R. C. Comprehensive Organic Transformation;
VCH: New York, 1989, pp 548–552.
2. (a) Kanth, J. V. B.; Periasamy, M. J. Org. Chem. 1991, 56,
5964–5965; (b) Prasad, A. S. B.; Kanth, J. V. B.;
Periasamy, M. Tetrahedron 1992, 48, 4623–4628.
3. Suseela, Y.; Periasamy, M. Tetrahedron 1992, 48, 371–376.
4. Cha, J. S.; Brown, H. C. J. Org. Chem. 1993, 58, 3974–
3979.
5. Ranu, B. C.; Das, A. R. J. Chem. Soc., Perkin Trans. 1
1992, 1561–1562.
6. Kamochi, Y.; Kudo, T. Tetrahedron Lett. 2000, 41, 341–
344.
7. Tale, R. H.; Patil, K. M.; Dapurkar, S. E. Tetrahedron
Lett. 2003, 44, 3427–3428.
31. Schauble, J. H.; Walter, G. J.; Morin, J. G. J. Org. Chem.
1974, 39, 755–760.
8. Ranu, B. C.; Basu, M. K. Tetrahedron Lett. 1991, 32,
3243–3246.
32. Excess NaBH4 (50%) was used for the reactions in entries
8, 11 and 13.
9. Berk, S. C.; Buchwald, S. L. J. Org. Chem. 1992, 57, 3751–
3753.