LETTER
Reaction of PhSeCl or PhSCl with 2,3-Allenoic Acids
87
Table 2 Cyclization of PhSeCl with 2,3-Allenoic Acidsa
A. G.; Cass, Q. B.; Pirani, J. R. Phytochemistry 1998, 49,
2493. (e) Otsuka, H.; Kotani, K.; Bando, M.; Kido, M.;
Takeda, Y. Chem. Pharm. Bull. 1998, 46, 1180. (f) Guo, S.;
Wang, L.; Chen, D. Indian J. Chem., Sect. B 1997, 36, 339.
(g) Evidente, A.; Sparapano, L. J. Nat. Prod. 1994, 57,
1720. (h) Damtoft, S.; Jensen, S. R. Phytochemistry 1995,
40, 157. (i) Estevez-Reyes, R.; Estevez-Braun, A.;
Gonzalez, A. G. J. Nat. Prod. 1993, 56, 1177. (j) Claydon,
N.; Hanson, J. R.; Truneh, A.; Avent, A. G. Phytochemistry
1991, 30, 3802. (k) Seki, T.; Satake, M.; Mackenzie, L.;
Kaspar, H. F.; Yasumoto, T. Tetrahedron Lett. 1995, 36,
7093. (l) Cambie, R. C.; Bergquist, P. R.; Karuso, P. J. Nat.
Prod. 1988, 51, 1014. (m) Ahmed, M.; Ahmed, A. A.
Phytochemistry 1990, 29, 2715. (n) De Guzman, F. S.;
Schmitz, F. J. J. Nat. Prod. 1990, 53, 926.
PhSe
R3
R1
R2
R3
N2, 0 °C
CH3CN
R1
R2
+
PhSeCl
O
COOH
O
1
2
Entry
1
Time Isolated
(h)
yield (%)
R1
R2
H
H
H
H
H
H
H
R3
1
2
3
4
5
6
7
8
n-C4H9
n-C7H15
Ph
H (1a)
19
14
10.5
10
11
10.5
7
91 (2a)
92 (2b)
77 (2c)
98 (2d)
90 (2e)
84 (2f)
98 (2g)
94 (2h)
H (1b)
(5) (a) Deshong, P.; Sidler, D. R.; Slough, G. A. Tetrahedron
Lett. 1987, 28, 2233. (b) Canonne, P.; Akssira, M.; Lemay,
G. Tetrahedron Lett. 1983, 24, 1929. (c) Schmit, C.;
Sahraoui-Taleb, S.; Differding, E.; Lombaert, C. G. D.;
Ghosez, L. Tetrahedron Lett. 1984, 25, 5043. (d) Cottier,
L.; Descotes, G.; Nigay, H.; Parron, J.; Gregoire, V. Bull.
Soc. Chim. Fr. 1986, 844. (e) Marshall, J. A.; Wolf, M. A. J.
Org. Chem. 1996, 61, 3238. (f) Yu, W.; Alper, H. J. Org.
Chem. 1997, 62, 5684. (g) Xiao, W.; Alper, H. J. Org.
Chem. 1997, 62, 3422. (h) Cowell, A.; Stille, J. K.
Tetrahedron Lett. 1979, 133. (i) Arcadi, A.; Bernocchi, E.;
Burini, A.; Cacchi, S.; Marinelli, F.; Pietroni, B.
CH3 (1c)
n-C3H7 (1d)
H (1e)
Ph
cyclohexyl
Ph
Bn (1f)
a-Naphthyl
(CH2)5
n-C3H7 (1g)
CH3 (1h)
8
a The reaction was carried out using 0.2–0.4 mmol of 2,3-allenoic
acid.
Tetrahedron 1988, 44, 481. (j) Marshall, J. A.; Bartley, G.
S.; Wallace, E. M. J. Org. Chem. 1996, 61, 5729.
(k) Clough, J. M.; Pattenden, G.; Wight, P. G. Tetrahedron
Lett. 1989, 30, 7469. (l) Gill, G. B.; Idris, M. S. H.
Tetrahedron Lett. 1985, 26, 4811. (m) Kejian, C.; Sanner,
M. A.; Carlson, R. M. Synth. Commun. 1990, 20, 901.
(n) Marshall, J. A.; Wallace, E. M.; Coan, P. S. J. Org.
Chem. 1995, 60, 796. (o) Yoneda, E.; Kaneko, T.; Zhang,
S.; Onitsuka, K.; Takahashi, S. Org. Lett. 2000, 2, 441.
(6) (a) Ma, S.; Yu, Z. Angew. Chem. Int. Ed. 2002, 41, 1775.
(b) Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387. (c) Ma,
S.; Duan, D.; Shi, Z. Org. Lett. 2000, 2, 1419. (d) Ma, S.;
Shi, Z.; Wu, S. Tetrahedron: Asymmetry 2001, 12, 193.
(e) Ma, S.; Duan, D.; Wang, Y. J. Comb. Chem. 2002, 4,
239. (f) Ma, S.; Shi, Z. Chem. Commun. 2002, 540.
(7) (a) Ma, S.; Yu, Z.; Wu, S. Tetrahedron 2001, 57, 1585.
(b) For Ag+-catalyzed cycloisomerization of 2,3-allenoic
acids, see: Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J.
Org. Chem. 1997, 62, 367. (c) For H+-catalyzed
Table 3 Cyclization of PhSCl with 2,3-Allenoic Acidsa
PhS
R1
R2
R3
R1
R2
R3
N2, 0 °C
CH3CN
+
PhSCl
O
COOH
O
1
3
Entry
1
Time Isolated
(h)
yield (%)
R1
R2
H
H
H
H
H
R3
1
2
3
4
5
6
n-C4H9
n-C7H15
Ph
H (1a)
9.5
49 (3a)
71 (3b)
95 (3c)
77 (3d)
82 (3e)
61 (3f)
H (1b)
10.5
8
cycloisomerization of 2,3-allenoic acids, see: Kresze, G.;
Kloimstein, L.; Runge, W. Liebigs Ann. Chem. 1976, 979.
(d) Also see: Musierowicz, S.; Wroblewski, A. E.
CH3 (1c)
H (1e)
cyclohexyl
Ph
9
Tetrahedron 1978, 34, 461.
(8) Ma, S.; Wu, S. J. Org. Chem. 1999, 64, 9314.
(9) Ma, S.; Wu, S. Chem. Commun. 2001, 441.
Bn (1f)
CH3 (1h)
19.5
9
(10) Ma, S.; Shi, Z.; Yu, Z. Tetrahedron Lett. 1999, 40, 2393.
(11) Ma, S.; Shi, Z.; Yu, Z. Tetrahedron 1999, 55, 12137.
(12) Ma, S.; Shi, Z. Chin. J. Chem. 2001, 19, 1280.
(13) Gill et al. reported the cyclization of 2,3-heptadienoic acid
with 1.1 equiv of phenylselenenyl chloride or phenylsulfenyl
chloride in CH2Cl2 at –78 °C affording the corresponding
product in 34% and 12%, respectively. See: Gill, G. B.; Idris,
M. S. H. Tetrahedron Lett. 1985, 26, 4811.
(CH2)5
a The reaction was carried out using 0.2–0.4 mmol of 2,3-allenoic
acid.
(4) For some of the most recent examples, see: (a) Chia, Y.;
Chang, F.; Wu, Y. Tetrahedron Lett. 1999, 40, 7513.
(b) Takahashi, S.; Maeda, K.; Hirota, S.; Nakata, T. Org.
Lett. 1999, 1, 2025. (c) Siddiqui, B. S.; Afshan, F.;
(14) 2,3-Allenoic acids were prepared according to the known
procedures: Clinet, J.-C.; Linstrumelle, G. Synthesis 1981,
875; see also ref.8.
Ghiasuddin Faizi, S.; Naqvi, S. N.-H.; Tariq, R. M. J. Chem.
Soc., Perkin Trans. 1 1999, 2367. (d) Cortez, D. A. G.;
Fernandes, J. B.; Vieria, P. C.; Silva, M. F. G. F.; Ferreira,
Synlett 2004, No. 1, 85–88 © Thieme Stuttgart · New York