S. Chandrasekhar et al. / Tetrahedron Letters 43 (2002) 3801–3803
3803
3. For epoxide opening with amines: (a) Reddy, L. R.;
Reddy, M. A.; Bhanumathi, N.; Rao, K. R.; New. J.
Chem. 2001, 221 [InCl3]; (b) Iqbal, J.; Pandey, A. Tetra-
hedron Lett. 1990, 31, 575 [CoCl2]; (c) Chini, M.; Crotti,
P.; Macchia, F. Tetrahedron Lett. 1990, 31, 4661 [CaCl2
and ZnCl2]; (d) Chandrasekhar, S.; Ramachandar, T.;
Prakash, S. J. Synthesis 2000, 1817 [TaCl5]; (e) Fu, X.-L.;
Wu, S.-H. Synth Commun. 1997, 27, 1677 [SmCl3]; (f) de
Weghe, P. V.; Collin, J. Tetrahedron Lett. 1995, 36, 1649
[SmI2].
amide]; (d) Yamada, J. I.; Yumoto, M.; Yamamoto, Y.
Tetrahedron Lett. 1989, 30, 4255 [Pb amide]; (e) Posner,
G. H.; Rogers, Z. J. Am. Chem. Soc. 1997, 99, 208
[amines absorbed on alumina]; (f) Reetz, M. T.; Binder, J.
Tetrahedron Lett. 1989, 30, 5425 [Al2O3]; (g) Onaka, M.;
Kawai, M.; Izumi, Y. Chem. Lett. 1985, 779 [zeolite].
9. For epoxide opening with thiols: (a) McGarvey, G. J.;
Mathys, J. A.; Wilson, K. J.; Overly, K. R.; Buonora, P.
T.; Spoors, P. G. J. Org. Chem. 1995, 60, 7778 [NaOH];
(b) Yamada, O.; Ogasawara, K. Synlett 1995, 427 [NaH];
(c) Yoon, N. M.; Choi, J.; Ahn, J. H. J. Org. Chem. 1994,
59, 3490 [BER]; (d) Raubo, P.; Wicha, J. Synlett 1993, 25
[SiO2]; (e) Chini, M.; Crotti, P.; Giovani, E.; Macchia, F.;
Pineschi, M. Synlett 1992, 303 [LiClO4 and Et3N]; (f)
Nishikubo, T.; Iizawa, T.; Shimojo, M.; Kato, T.; Shina,
A. J. Org. Chem. 1990, 55, 2536 [n-Bu4NBr]; (g)
Yamashita, H.; Mukaiyama, T. Chem. Lett. 1985, 1643
[cat. Zn-tartarate].
4. For epoxide opening with thiols: Lay, L.; Nicotra, F.;
Panza, L.; Russo, G. Synlett 1995, 167 [ZnCl2].
5. For epoxide opening with alcohols: China, M.; Critti, P.;
Flippin, L. A.; Macchia, F.; Pineschi, M. J. Org. Chem.
1992, 57, 1405 [Zn(OTf)2].
6. For epoxide opening with amines: (a) Sekar, G.; Singh,
V. K. J. Org. Chem. 1999, 64, 287 [Cu(OTf)2]; (b) Auge,
J.; Leroy, F. Tetrahedron Lett. 1996, 37, 7715 [LiOTf]; (c)
Chini, M.; Crotti, R.; Favero, L.; Macchia, F.; Pineschi,
M. Tetrahedron Lett. 1994, 35, 433 [La(OTf)3]; (d)
Meguro, N.; Asao, N.; Yamamoto, Y. J. Chem. Soc.,
Perkin Trans. 1 1994, 2597 [Yb(OTf)3]; (e) Fuziwara, M.;
Imada, M.; Baba, A.; Matsuda, H. Tetrahedron Lett.
1989, 30, 739 [Ph4SbOTf].
7. For epoxide opening with alcohols: (a) Ramachandran,
P. V.; Gong, B.; Brown, H. C. J. Org. Chem. 1995, 60, 41
[H2SO4]; (b) Thompson, D. H.; Svendsen, C. B.; Meglio,
C. D.; Anderson, V. C. J. Org. Chem. 1994, 59, 2945
[CF3SO3H]; (c) Ramesh, K.; Wolfe, M. S.; Lee, Y.;
Velde, D. V.; Borchardt, R. T. J. Org. Chem. 1992, 57,
5861 [10-CSA]; (d) Jones, R. J.; Rapport, H. J. Org.
Chem. 1990, 55, 1144 [HClO4]; (e) Chini, M.; Crotti, P.;
Flippin, L. A.; Macchia, F. J. Org. Chem. 1990, 55, 4165
[LiClO4]; (f) Jaramillo, C.; Chiara, J.-L.; Martin-Lomas,
M. J. Org. Chem. 1994, 59, 3135 [BF3Et2O]; (g) Otera, J.;
Niibo, Y.; Tatsuui, N.; Nozaki, H. J. Org. Chem. 1988,
53, 275 [Organotin phosphate condensates]; (h) Olah, G.;
Fung, A. P.; Meidar, D. Synthesis 1981, 281 [Nalfion-H];
(i) Masaki, Y.; Miura, T.; Ochiai, M. Synlett 1993, 847
[TCNE]; (j) Iranpoor, N.; Mohammadpour Baltork, I.
Tetrahedron Lett. 1990, 31, 735 [DDQ]; (k) Iranpoor, N.;
Mohammadpour Baltork, I. Synth. Commun. 1990, 20,
2789 [CAN].
10. Blackwell, J. M.; Piers, W. E.; Parvez, M. Org. Lett.
2000, 2, 695.
11. For recent review on the use of B(C6F5)3 and analogues
as co-catalysts in metal catalyzed olefin polymerization,
see: (a) Chen, E. Y.-X.; Marks, T. J. Chem. Rev. 2000,
100, 1391. For the use of B(C6F5)3 as a catalyst: Rubin,
M.; Gevorgyan, V. Org. Lett. 2001, 3, 2705 and refer-
ences cited therein.
12. (a) In the case of entry 1 and 5, the cleavage products
were confirmed by acetylation and oxidation; (b) Spectral
data for selected products: (3d): 1H NMR (CDCl3, 200
MHz): l 7.4–7.12 (m, 10H), 4.5 (s, 2H), 3.94–3.8 (m, 1H),
3.58–3.46 (m, 2H), 3.1–3 (m, 2H); IR (neat): 3623, 2876,
2832, 866 cm−1; EIMS (m/z): 274 (M+), 123, 91, 43. (5b):
1H NMR (CDCl3, 300 MHz): l 7.74–7.6 (m, 3H), 7.45–
7.2 (m, 2H), 7.18–7.02 (m, 2H), 4.42–4.36 (m, 1H), 4.22
(d, J=1.2 Hz, 2H), 4.18–4.1 (m, 2H), 3.8–3.66 (m, 2H),
2.42–2.38 (m, 1H); IR (KBr): 3622, 3312, 2132, 766 cm−1
;
EIMS (m/z): 256 (M+), 144, 115, 69. (6b): 1H NMR
(CDCl3, 200 MHz): l 7.36–7.1 (m, 5H), 4.26–4.18 (m,
1H), 3.98–3.4 (m, 5H), 2.65 (t, J=8.5 Hz, 2H), 2.42–2.34
(m, 1H), 1.96–1.6 (m, 4H), 0.92 (s, 9H), 0.1 (s, 6H); IR
(neat): 3624, 3318, 2140, 1276, 853 cm−1; EIMS (m/z):
362 (M+), 249, 117, 91. (7a): 1H NMR (CDCl3, 200
MHz): l 7.4–7.2 (m, 5H), 5.98–5.74 (m, 1H), 5.3–5.06 (m,
3H), 4.78 (d, J=4.3 Hz, 1H), 4.04–3.92 (m, 3H), 3.7–3.58
(m, 2H), 3.5–3.36 (m, 2H), 1.78–1.52 (m, 6H); IR (neat):
3626, 2890, 1436, 935 cm−1; EIMS (m/z): 191 (M+−101),
101, 85, 41.
8. For epoxide opening with amines: (a) Chini, M.; Crotti,
P.; Macchia, F. J. Org. Chem. 1991, 56, 5939 [metal
salts]; (b) Reddy, L. R.; Reddy, M. A.; Bhanumathi, N.;
Rao, K. R. Synlett 2000, 339 [cyclodextrin]; (c) Overman,
L. E.; Flippin, L. A. Tetrahedron Lett. 1981, 22, 175 [Al