L.-J. Zhao et al. / Tetrahedron 61 (2005) 12026–12032
12031
Park, J. C.; Yoo, J. U. Helv. Chim. Acta 2002, 85, 3994–3999.
(c) Anand, R. V.; Baktharaman, S.; Singh, V. K. Tetrahedron
Lett. 2002, 43, 5393–5395. (d) Dunn, P. J.; Hughes, M. L.;
Searle, P. M.; Wood, A. S. Org. Process Res. Dev. 2003, 7,
244–253.
56 mg, 1.0 mmol, 2.0 equiv) were added to the suspension.
The reaction mixture was stirred at room temperature for the
indicated time or until TLC analysis indicated the
disappearance of 5. The reaction mixture was then diluted
with CH2Cl2 (7.0 mL) and the catalyst was filtered off and
recovered. The filtrate was concentrated under reduced
pressure and the residue was purified by column chroma-
tography (20% EtOAc/petroleum ether) to afford the desired
product 9. Characterization data for these products was
consistent with previously reported data.6m
5. (a) Shi, M.; Jiang, J.-K.; Feng, Y.-S. Org. Lett. 2000, 2,
2397–2400. (b) Shi, M.; Feng, Y.-S. J. Org. Chem. 2001, 66,
406–411. (c) Shi, M.; Li, C.-Q.; Jiang, J.-K. Chem. Commun.
2001, 833–834.
6. (a) Shi, M.; Xu, Y.-M. Chem. Commun. 2001, 1876–1877.
(b) Shi, M.; Xu, Y.-M. Eur. J. Org. Chem. 2002, 696–701. (c)
Shi, M.; Xu, Y.-M.; Zhao, G.-L.; Wu, X.-F. Eur. J. Org. Chem.
2002, 3666–3679. (d) Shi, M.; Xu, Y.-M. J. Org. Chem. 2003,
68, 4784–4790. (e) Shi, M.; Xu, Y.-M. Angew. Chem., Int. Ed.
2002, 41, 4507–4510. (f) Shi, M.; Chen, L.-H. Chem.
Commun. 2003, 1310–1311. (g) Zhao, G.-L.; Huang, J.-W.;
Shi, M. Org. Lett. 2003, 5, 4737–4739. (h) Xu, Y.-M.; Shi, M.
J. Org. Chem. 2004, 69, 417–425. (i) Shi, M.; Zhao, G.-L.
Tetrahedron 2004, 60, 2083–2089. (j) Shi, M.; Zhao, G.-L.
Adv. Synth. Catal. 2004, 346, 1205–1219. (k) Shi, Y.-L.;
Xu, Y.-M.; Shi, M. Adv. Synth. Catal. 2004, 346, 1220–1230.
(l) Shi, M.; Xu, Y.-M.; Shi, Y.-L. Chem. Eur. J. 2005, 11,
1794–1802. (m) Shi, M.; Chen, L.-H.; Li, C.-Q. J. Am. Chem.
Soc. 2005, 127, 3790–3800.
4.6. General procedure for the JJ-OMe-PPh3 (1f)
catalyzed AMBH reactions of N-sulfonated imines (5)
with phenyl acrylate (10)
JJ-OMe-PPh3 (1f, 0.05 mmol) was added to dry THF
(1.0 mL) under an argon atmosphere and the suspension was
stirred for 1 h at room temperature (swelling time). At this
time, the N-sulfonated imine 5 (0.5 mmol) and 10 (89 mg,
0.6 mmol, 1.2 equiv) were added to the suspension. The
reaction mixture was stirred at room temperature for the
indicated time. The reaction mixture was then diluted with
CH2Cl2 (7.0 mL) and the catalyst was filtered off and
recovered. The filtrate was concentrated under reduced
pressure and the residue was purified by column chroma-
tography (12.5% EtOAc/petroleum ether) to afford the
desired product 11. Characterization data for these products
was consistent with previously reported data.6f
7. For related work by others concerning the aza-Baylis–Hillman
reaction, see: (a) Perlmutter, P.; Teo, C. C. Tetrahedron Lett.
1984, 25, 5951–5952. (b) Bertenshaw, S.; Kahn, M.
Tetrahedron Lett. 1989, 30, 2731–2732. (c) Takagi, M.;
Yamamoto, K. Tetrahedron 1991, 47, 8869–8882. (d) Campi,
E. M.; Holmes, A.; Perlmutter, P.; Teo, C. C. Aust. J. Chem.
1995, 48, 1535–1540. (e) Kamimura, A.; Gunjigake, Y.;
Mitsudera, H.; Yokoyama, S. Tetrahedron Lett. 1998, 39,
7323–7324. (f) Balan, D.; Adolfsson, H. J. Org. Chem. 2001,
66, 6498–6501. (g) Balan, D.; Adolfsson, H. J. Org. Chem.
2002, 67, 2329–2334. (h) Balan, D.; Adolfsson, H. Tetra-
Acknowledgements
This research was supported financially by the University of
Hong Kong, the Research Grants Council of the Hong Kong
Special Administrative Region, People’s Republic of China
(Project No. HKU 7027/03P), the State Key Project of Basic
Research (Project 973, no. G2000048007), the Shanghai
Municipal Committee of Science and Technology, and the
National Natural Science Foundation of China (Nos.
20025206, 203900502, and 20272069).
`
hedron Lett. 2003, 44, 2521–2524. (i) Ribiere, P.; Enjalbal, C.;
Aubagnac, J.-L.; Yadav-Bhatnagar, N.; Martinez, J.; Lamaty,
`
F. J. Comb. Chem. 2004, 6, 464–467. (j) Declerck, V.; Ribiere,
P.; Martinez, J.; Lamaty, F. J. Org. Chem. 2004, 69,
8372–8381. (k) Matsui, K.; Takizawa, S.; Sasai, H. J. Am.
Chem. Soc. 2005, 127, 3680–3681.
8. For a review of polymer-supported organic catalysts, see:
Benaglia, M.; Puglisi, A.; Cozzi, F. Chem. Rev. 2003, 103,
3401–3430.
References and notes
9. For general reviews of polymer-supported reagents and
catalysts, see: (a) Ley, S. V.; Baxendale, I. R.; Bream, R. N.;
Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.;
Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin
Trans. 1 2000, 3815–4195. (b) Kirschning, A.; Monenschein,
H.; Wittenberg, R. Angew. Chem., Int. Ed. 2001, 40, 650–679.
(c) Clapham, B.; Reger, T. S.; Janda, K. D. Tetrahedron 2001,
57, 4637–4662. (d) Leadbeater, N. E.; Marco, M. Chem. Rev.
2002, 102, 3217–3274. (e) McNamara, C. A.; Dixon, M. J.;
Bradley, M. Chem. Rev. 2002, 102, 3275–3300. (f) Fan, Q.-H.;
Li, Y.-M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385–3466.
1. (a) Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996,
52, 8001–8062. (b) Ciganek, E. Org. React. 1997, 51,
201–350. (c) Langer, P. Angew. Chem., Int. Ed. 2000, 39,
3049–3052. (d) Kim, J. N.; Lee, K. Y. Curr. Org. Chem. 2002,
6, 627–645. (e) Basavaiah, D.; Rao, A. J.; Satyanarayana, T.
Chem. Rev. 2003, 103, 811–892.
2. (a) Hill, J. S.; Isaacs, N. S. J. Phys. Org. Chem. 1990, 3,
285–288. (b) Santos, L. S.; Pavam, C. H.; Almeida, W. P.;
Coelho, F.; Eberlin, M. N. Angew. Chem., Int. Ed. 2004, 43,
4330–4333. (c) Aggarwal, V. K.; Fulford, S. Y.; Lloyd-Jones,
G. C. Angew. Chem., Int. Ed. 2005, 44, 1706–1708. (d) Price,
K. E.; Broadwater, S. J.; Jung, H. M.; McQuade, D. T. Org.
Lett. 2005, 7, 147–150.
¨
(g) Brase, S.; Lauterwasser, F.; Ziegert, R. E. Adv. Synth.
Catal. 2003, 345, 869–929. (h) Bhattacharyya, S. Curr. Opin.
Drug Discov. Dev. 2004, 752–764.
10. Toy, P. H.; Reger, T. S.; Janda, K. D. Org. Lett. 2000, 2,
2205–2207.
3. Aggarwal, V. K.; Emme, I.; Fulford, S. Y. J. Org. Chem. 2003,
68, 692–700.
11. Lau, K. C. Y.; He, H. S.; Chiu, P.; Toy, P. H. J. Comb. Chem.
2004, 6, 955–960.
4. (a) Trost, B. M.; Thiel, O. R.; Tsu, H.-C. J. Am. Chem. Soc.
2002, 124, 11616–11617. (b) Cho, J.-H.; Ko, S. Y.; Oh, E.;