4452
J. Blanchet, J. Zhu / Tetrahedron Letters 45 (2004) 4449–4452
8
. (a) Majcen le Mar ꢀe chal, A.; Robert, A.; Leban, I.
Tetrahedron 1990, 46, 453–464; (b) Jaguelin, S.; Robert,
A.; Gayral, P. Eur. J. Chem. 1991, 26, 51–57.
. Reaction with thioamide, see: (a) Ferrey, M.; Robert, A.;
Foucaud, A. Synthesis 1976, 261–262; (b) Baudy, M.;
Robert, A.; Foucaud, A. J. Org. Chem. 1978, 43, 3732–3736;
solid. Pure thiazolone 4b was precipitated from EtOAc/
heptane as a white solid (160 mg, 81% yield).
16. Herr, R. J.; Kulher, J. L.; Meckler, H.; Opalka, C. J.
Synthesis 2000, 1569–1574.
17. Among various conditions examined, this procedure turns
out to be the most reproducible and versatile in our hands.
(a) Corey, E. J.; Link, J. O.; Shao, Y. Tetrahedron Lett.
1992, 3435–3438; (b) Wang, Z.; Campagna, S.; Yang, K.;
Xu, G.; Pierce, M. E.; Fortunak, J. M.; Confalone, P. N.
J. Org. Chem. 2000, 65, 1889–1891.
9
(
c) Baudy-Floc’h, M.; Robert, A. Synthesis 1981, 981–983.
0. Zhu, J. Eur. J. Chem. 2003, 1133–1144.
1
1
1. Selected examples: (a) Reeve, W.; Woods, C. W. J. Am.
Chem. Soc. 1960, 82, 4062–4066; (b) Reeve, W.; Fine, L.
W. J. Org. Chem. 1964, 29, 1148–1150; (c) Benner, J. P.;
Gill, G. B.; Parrott, S. J.; Wallace, B. J. Chem. Soc.,
Perkin Trans. 1 1984, 331–342; (d) Corey, E. J.; Link, J. O.
J. Am. Chem. Soc. 1992, 114, 1906–1908.
2. Reeve, W.; Nees, M. J. Am. Chem. Soc. 1967, 89, 647–651.
3. For a review, see: Reeve, W. Synthesis 1981, 131–138.
4. (a) Hebert, P. Bull. Soc. Chim. Fr. 1920, 27, 45–55; (b)
Weizmann, C.; Sulzbacher, M.; Bergmann, E. J. Am.
Chem. Soc. 1948, 70, 1153–1158; (c) Bergmann, E. D.;
Ginsburg, D.; Lavie, D. J. Am. Chem. Soc. 1950, 72, 5012–
18. Araki, S.; Ho, H.; Butsugan, Y. J. Org. Chem. 1988, 53,
1831–1833.
1
19. In DMSO-d , the HNMR spectra of 4g displayed 2NH
signals around 9.27, 9.01 ppm, respectively, corresponding
to the zwitterionic form of the imino thiazolidinone. 2-
6
1
1
1
Imino-5-naphthalen-2-yl-thiazolidin-4-one 4g:
R
f
:
(EtOAc); FTIR (KBr): 3048, 1633, 1505, 1359, 1269,
0.3
ꢀ
1
1
1235, 1168, 1123, 1082 cm
[(CD SO)] d 9.27 (s, 1H), 9.01 (s, 1H), 7.89 (m, 4H),
7.53 (m, 2H), 7.29 (d, 1H, J ¼ 7.1 Hz), 5.61 (s, 1H);
NMR (62.5 MHz, (CD SO) d 187.9, 181.5, 135.0, 132.8,
132.4, 128.6, 127.7, 127.6, 126.6, 126.4, 125.6 (2C), 59.4;
HRMS (EI) calcd for C13 OSNa 265.0412, found
;
H NMR (300 MHz,
3 2
)
1
3
C
5014; (d) Reeve, W.; Woods, W. J. Am. Chem. Soc. 1960,
3 2
)
82, 4062–4066.
1
5. Typical experimental procedure: To a vigorously stirred
solution of carbinol 9b (232 mg, 1.0 mmol) and thiourea
10 2
H N
265.0429; mp (EtOAc/heptane) 165 °C.
20. For a one-pot synthesis of a-methoxyphenylacetic acid
from aldehyde via phenyltrichloromethyl carbinol, see:
Reeve, W.; Compere, E. L. J. Am. Chem. Soc. 1961, 83,
2755–2759.
(152 mg, 2 equiv) in 2 mL of DME is added at 0 °C a
solution of 8 mL of 0.5 M aqueous NaOH (4 equiv) over
2
1
0 min. The cloudy monophasic solution is well stirred for
2 h at room temperature and the reaction is neutralized
with dilute hydrochloric acid. The aqueous layer is
extracted with ethyl acetate. The organic layers are
combined, washed with water and brine, dried over
21. Wyvratt, J. M.; Hazen, G. C.; Weinstock, L. M. J. Org.
Chem. 1987, 52, 944–945.
22. Aggarwal, V.; Mereu, A. J. Org. Chem. 2000, 65, 7211–
7212.
2 4
Na SO and evaporated to furnish a slightly coloured