V. Kumar et al. / Tetrahedron 63 (2007) 9718–9723
9723
3. (a) Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34,
633–639; (b) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev.
2002, 102, 1731–1769; (c) Pavan, C.; Legros, J.; Bolm, C.
Adv. Synth. Catal. 2005, 347, 703–705.
Synth. Catal. 2006, 348, 354–360; (g) Sinha, A. K.; Joshi,
B. P.; Sharma, A.; Kumar, V.; Acharya, R. Aust. J. Chem.
2007, 60, 124–127; (h) Sinha, A. K.; Sharma, A.; Joshi, B. P.
Tetrahedron 2007, 63, 960–965.
4. (a) Sutarjadi, N. F.; Dyatmiko, W.; Rahman, A.; Hoastettmann,
K. Phytochemistry 1995, 39, 409–412; (b) Naemura, K.;
Murata, M.; Tanaka, R.; Yano, M.; Hirose, K.; Tobe, Y.
Tetrahedron: Asymmetry 1996, 7, 3285–3294; (c) Kamal, A.;
Sandbhor, M.; Ramana, K. V. Tetrahedron: Asymmetry 2002,
13, 815–820; (d) Goswami, A.; Goswami, J. Tetrahedron
11. (a) Carrillo, J. R.; Ortiz, A. D.; Hoz, A. D. L.; Escalonilla,
M. J. G.; Moreno, A.; Prieto, P. Tetrahedron 1999, 55, 9623–
9630; (b) Perreux, L.; Loupy, A. Tetrahedron 2001, 57,
9199–9223.
12. (a) Walker, D.; Heibert, J. Chem. Rev. 1967, 67, 153–195; (b)
Bharate, S. B. Synlett 2006, 469–497; (c) Zhang, A. Y.; Li,
C.-J. J. Am. Chem. Soc. 2006, 128, 4242–4243.
ꢀ
Lett. 2005, 46, 4411–4413; (e) Kowalski, J.; P1oszynska, J.;
Sobkowiak, A.; Morzycki, J. W.; Wilczewska, A. Z.
J. Electroanal. Chem. 2005, 585, 275–280; (f) Radnik, J.;
Benhmid, A.; Kalevaru, V. N.; Pohl, M. M.; Martin, A.;
13. (a) Sinha, A. K.; Acharya, R.; Joshi, B. P. J. Nat. Prod. 2002,
65, 764–765; (b) Joshi, B. P.; Sharma, A.; Sinha, A. K.
Tetrahedron 2005, 61, 3075–3080; (c) Joshi, B. P.; Sharma,
A.; Sinha, A. K. Can. J. Chem. 2005, 83, 1826–1832; (d)
Sinha, A. K.; Joshi, B. P.; Acharya, R. US Patent 6,969,778,
2005; (e) Joshi, B. P.; Sharma, A.; Sinha, A. K. Tetrahedron
2006, 62, 2590–2593; (f) Sinha, A. K.; Sharma, A.; Swaroop,
A.; Kumar, V. Tetrahedron 2007, 63, 1000–1007.
14. Chandrashekhar, S.; Sumithra, G.; Yadav, J. S. Tetrahedron
Lett. 1996, 37, 1645–1646.
15. (a) Lee, H.; Harvey, R. G. J. Org. Chem. 1983, 48, 749–751; (b)
Lehr, R. E.; Kole, P. L.; Tschappat, K. D. Tetrahedron Lett.
1986, 27, 1649–1652; (c) Lee, H. R.; Harvey, G. J. Org.
Chem. 1988, 53, 4587–4589.
€
Lucke, B.; Dingerdissen, U. Angew. Chem., Int. Ed. 2005, 44,
6771–6774; (g) Matasuda, H.; Ando, S.; Morikawa, T.;
Kataoka, S.; Yoshikawa, M. Bioorg. Med. Chem. Lett. 2005,
15, 1949–1953; (h) Shaikh, T. M. A.; Sudalai, A. Tetrahedron
Lett. 2005, 46, 5587–5590; (i) Fuglseth, E.; Anthonsen, T.;
Hoff, B. H. Tetrahedron: Asymmetry 2006, 17, 1290–1295;
(j) Raminelli, C.; Kagohara, E.; Pellizari, V. H.; Comasseto,
J. V.; Andrade, L. H.; Porto, A. L. M. Enzyme Microb.
Technol. 2007, 40, 362–369.
5. (a) Hamachi, K.; Irie, R.; Katsuki, T. Tetrahedron Lett. 1996,
37, 4979–4982; (b) Hie, T. H. R.; Mihara, J.; Hamachi, K.;
Katsuki, T. Tetrahedron 1998, 54, 10017–10028.
6. (a) Yoshizumi, T.; Takaya, H. Tetrahedron: Asymmetry 1995, 6,
1253–1256; (b) Lin, G.; Lin, W. Y. Tetrahedron Lett. 1998, 39,
4333–4336; (c) Koul, S.; Taneja, S. C.; Parshad, R.; Qazi, G. N.
Tetrahedron: Asymmetry 1998, 9, 3395–3399.
16. (a) Luche, J. L. Ultrasonics 1990, 28, 316–321; (b) Luche,
J. L.; Einhorn, C.; Einhorn, J.; Sinisterra-Gago, J. V.
Tetrahedron Lett. 1990, 31, 4125–4128; (c) Ando, T.;
^
Kimura, T.; Leveque, J.-M.; Lorimer, J. P.; Luche, J.-L.;
Mason, T. J. J. Org. Chem. 1998, 63, 9561–9564; (d)
^
Kimura, T.; Harada, H.; Ando, T.; Fujita, M.; Leveque, J. M.;
Luche, J. L. Chem. Commun. 2002, 1174–1175.
7. (a) Riley, R. F. J. Am. Chem. Soc. 1950, 72, 5712–5714; (b)
Nobutoshi, I. Nippon Kagaku Kaishi 1950, 71, 235–239; (c)
Ludwig, C. H.; Nist, B. J.; McCarthy, J. L. J. Am. Chem. Soc.
1964, 86, 1186–1196; (d) Glasser, W. G. Polymer 1973, 14,
395–397; (e) Pisova, M.; Pospisek, J.; Soucek, M. Collect.
Czech. Chem. Commun. 1975, 40, 1768–1774; (f) Gordon, L.
Aust. J. Chem. 1977, 30, 1133–1136; (g) Bouquet, M.; Guy,
A.; Lemaire, M.; Guette, J. P. Synth. Commun. 1985, 15,
1153–1157; (h) Iiyama, K.; Wallis, A. F. A. J. Wood Chem.
Tech. 1990, 10, 39–58; (i) Giuseppe, P.-F.; Stefano, S.
J. Chem. Soc., Perkin Trans. 1 1992, 1029–1033.
17. (a) Ramdayal, F. D.; Kiemle, D. J.; LaLonde, R. T. J. Org.
Chem. 1999, 64, 4607–4609; (b) Wang, W.; Li, T.; Attardo,
G. J. Org. Chem. 1997, 62, 6598–6602.
18. (a) Becker, H. D. J. Org. Chem. 1969, 34, 1203–1207; (b)
Zhang, S.-L.; An, L.-K.; Huang, Z.-S.; Ma, L.; Li, Y.-M.;
Chan, A. S. C.; Gu, L.-Q. Tetrahedron 2005, 61, 3087–3090.
19. (a) DePuy, C. H.; Leary, R. E. J. Am. Chem. Soc. 1957, 79,
3705–3709; (b) Smith, G. G.; Bagley, F. D.; Taylor, R. J. Am.
Chem. Soc. 1961, 83, 3647–3653; (c) Barrero, A. F.;
ꢀ
Herrador, M. M.; Quılez del Moral, J. F.; Arteaga, P.;
8. (a) Heiba, E. I.; Dessau, R. M.; Koehl, W. J., Jr. J. Am. Chem.
Soc. 1969, 91, 138–139; (b) Ganin, E.; Amer, I. J. Mol.
Catal. 1997, 116, 323–327; (c) Utley, J. H. P.; Rozenberg,
G. G. J. Appl. Electrochem. 2003, 33, 525–532; (d) Khenkin,
A. M.; Neumann, R. J. Am. Chem. Soc. 2004, 126, 6356–
6362; (e) Banerjee, A. K.; Vera, W.; Laya, M. S. Synth.
Commun. 2004, 34, 2301–2308.
ꢀ
Akssira, M.; Hanbali, F. E.; Arteaga, J. F.; Dieguez, H. R.;
Sanchez, E. M. J. Org. Chem. 2007, 72, 2251–2254.
ꢀ
20. Tetsuya, T.; Yoshiaki, A.; Seisho, T. Chem. Pharm. Bull. 1995,
43, 1970–1976.
21. The product benzylacetates and side products formed in
traces were estimated on the basis of 1H and 13C NMR
spectra, and by comparison of TLC, Co-TLC and physical
properties with the standard.4,7 The HRMS data of the ob-
tained acetoxylated products couldn’t be obtained as these
benzylic acetates underwent pyrolysis19,22 during the
HRMS analysis to give the corresponding arylalkenes13b as
base peak.
22. (a) Cruz, A.; Diaz, F.; Chamorro, G.; Tamariz, J.
Arzneimittelforschung 2001, 51, 535–544; (b) Jung, Y.-S.;
Jeo, B.-Y.; Seong, C.-M.; Park, N.-S. Synth. Commun. 2001,
31, 2735–2741.
9. Minisci, F.; Recupero, F.; Gambarotti, C.; Punta, C.; Paganelli,
R. Tetrahedron Lett. 2003, 44, 6919–6922.
10. (a) Thompson, L. H.; Doraiswamy, L. K. Ind. Eng. Chem. Res.
1999, 38, 1215–1249; (b) Hayes, B. L. Microwaves Synthesis:
Chemistry at the Speed of Light; CEM: Matthews, North
Carolina, 2002; (c) Ambulgekar, G. V.; Samant, S. D.;
Pandit, A. B. Ultrason. Sonochem. 2004, 11, 191–196; (d)
Leadbeater, N. E. Chem. Commun. 2005, 2881–2902; (e)
Peng, Y.; Zhong, W.; Song, G. Ultrason. Sonochem. 2005,
12, 169–172; (f) Sharma, A.; Kumar, V.; Sinha, A. K. Adv.