Indium trichloride (InCl3) catalysed Diels-Alder reaction in water

Chemical Communications

Volumn , Issue 20, 1996, Pages 2315-2316

  Loh, Teck Peng ^a   Pei, Jian ^a   Lin, Mei ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002983964     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/CC9960002315     Document Type: Article

References (17)

1. For examples of Diels-Alder reactions in water without catalyst, see D. C. Rideout and R. Breslow, J. Am. Chem. Soc., 1980, 102, 7816; S. D. Larsen and P. A. Grieco, J. Am. Chem. Soc., 1985, 107, 1768; P. A. Grieco and S. D. Larsen, Org. Synth., 1990, 68, 206; P. A. Grieco, S. D. Larsen and W. F. Fobare, Tetrahedron Lett., 1986, 27, 1975; P. A. Grieco, D. T. Parker, W. F. Fobare and R. Ruckle, J. Am. Chem. Soc., 1987, 109, 5859; P. A. Grieco and A. Bahsas, J. Org. Chem., 1987, 52, 5746; P. A. Grieco and J. D. Clark J. Org. Chem., 1990, 55, 2271.
2. For examples of Diels-Alder reactions in water without catalyst, see D. C. Rideout and R. Breslow, J. Am. Chem. Soc., 1980, 102, 7816; S. D. Larsen and P. A. Grieco, J. Am. Chem. Soc., 1985, 107, 1768; P. A. Grieco and S. D. Larsen, Org. Synth., 1990, 68, 206; P. A. Grieco, S. D. Larsen and W. F. Fobare, Tetrahedron Lett., 1986, 27, 1975; P. A. Grieco, D. T. Parker, W. F. Fobare and R. Ruckle, J. Am. Chem. Soc., 1987, 109, 5859; P. A. Grieco and A. Bahsas, J. Org. Chem., 1987, 52, 5746; P. A. Grieco and J. D. Clark J. Org. Chem., 1990, 55, 2271.
3. For examples of Diels-Alder reactions in water without catalyst, see D. C. Rideout and R. Breslow, J. Am. Chem. Soc., 1980, 102, 7816; S. D. Larsen and P. A. Grieco, J. Am. Chem. Soc., 1985, 107, 1768; P. A. Grieco and S. D. Larsen, Org. Synth., 1990, 68, 206; P. A. Grieco, S. D. Larsen and W. F. Fobare, Tetrahedron Lett., 1986, 27, 1975; P. A. Grieco, D. T. Parker, W. F. Fobare and R. Ruckle, J. Am. Chem. Soc., 1987, 109, 5859; P. A. Grieco and A. Bahsas, J. Org. Chem., 1987, 52, 5746; P. A. Grieco and J. D. Clark J. Org. Chem., 1990, 55, 2271.
4. For examples of Diels-Alder reactions in water without catalyst, see D. C. Rideout and R. Breslow, J. Am. Chem. Soc., 1980, 102, 7816; S. D. Larsen and P. A. Grieco, J. Am. Chem. Soc., 1985, 107, 1768; P. A. Grieco and S. D. Larsen, Org. Synth., 1990, 68, 206; P. A. Grieco, S. D. Larsen and W. F. Fobare, Tetrahedron Lett., 1986, 27, 1975; P. A. Grieco, D. T. Parker, W. F. Fobare and R. Ruckle, J. Am. Chem. Soc., 1987, 109, 5859; P. A. Grieco and A. Bahsas, J. Org. Chem., 1987, 52, 5746; P. A. Grieco and J. D. Clark J. Org. Chem., 1990, 55, 2271.
5. For examples of Diels-Alder reactions in water without catalyst, see D. C. Rideout and R. Breslow, J. Am. Chem. Soc., 1980, 102, 7816; S. D. Larsen and P. A. Grieco, J. Am. Chem. Soc., 1985, 107, 1768; P. A. Grieco and S. D. Larsen, Org. Synth., 1990, 68, 206; P. A. Grieco, S. D. Larsen and W. F. Fobare, Tetrahedron Lett., 1986, 27, 1975; P. A. Grieco, D. T. Parker, W. F. Fobare and R. Ruckle, J. Am. Chem. Soc., 1987, 109, 5859; P. A. Grieco and A. Bahsas, J. Org. Chem., 1987, 52, 5746; P. A. Grieco and J. D. Clark J. Org. Chem., 1990, 55, 2271.
6. For examples of Diels-Alder reactions in water without catalyst, see D. C. Rideout and R. Breslow, J. Am. Chem. Soc., 1980, 102, 7816; S. D. Larsen and P. A. Grieco, J. Am. Chem. Soc., 1985, 107, 1768; P. A. Grieco and S. D. Larsen, Org. Synth., 1990, 68, 206; P. A. Grieco, S. D. Larsen and W. F. Fobare, Tetrahedron Lett., 1986, 27, 1975; P. A. Grieco, D. T. Parker, W. F. Fobare and R. Ruckle, J. Am. Chem. Soc., 1987, 109, 5859; P. A. Grieco and A. Bahsas, J. Org. Chem., 1987, 52, 5746; P. A. Grieco and J. D. Clark J. Org. Chem., 1990, 55, 2271.
7. For examples of Diels-Alder reactions in water without catalyst, see D. C. Rideout and R. Breslow, J. Am. Chem. Soc., 1980, 102, 7816; S. D. Larsen and P. A. Grieco, J. Am. Chem. Soc., 1985, 107, 1768; P. A. Grieco and S. D. Larsen, Org. Synth., 1990, 68, 206; P. A. Grieco, S. D. Larsen and W. F. Fobare, Tetrahedron Lett., 1986, 27, 1975; P. A. Grieco, D. T. Parker, W. F. Fobare and R. Ruckle, J. Am. Chem. Soc., 1987, 109, 5859; P. A. Grieco and A. Bahsas, J. Org. Chem., 1987, 52, 5746; P. A. Grieco and J. D. Clark J. Org. Chem., 1990, 55, 2271.
8. For examples of lanthanide(III) catalysed Diels-Alder reactions in aqueous media, see K. Mikami, O. Kotera, Y. Motoyama and H. Sakaguchi, Synlett, 1995, 975; H. Sasai, T. Suzuki, N. Itoh, K. Tanaka, T. Date, K. Okamura and M. Shibazaki, Tetrahedron Lett., 1993, 34, 851; L. Yu, D. Chen and P. G. Wang, Tetrahedron Lett., 1996, 37, 2169; S. Kobayashi, I. Hachiya, M. Araki and H. Ishitani, Tetrahedron Lett., 1993, 34, 3755; S. Kobayashi, I. Hachiya, T. Takahori, M. Araki and H. Ishitani, Tetrahedron Lett., 1992, 33, 6825.
9. For examples of lanthanide(III) catalysed Diels-Alder reactions in aqueous media, see K. Mikami, O. Kotera, Y. Motoyama and H. Sakaguchi, Synlett, 1995, 975; H. Sasai, T. Suzuki, N. Itoh, K. Tanaka, T. Date, K. Okamura and M. Shibazaki, Tetrahedron Lett., 1993, 34, 851; L. Yu, D. Chen and P. G. Wang, Tetrahedron Lett., 1996, 37, 2169; S. Kobayashi, I. Hachiya, M. Araki and H. Ishitani, Tetrahedron Lett., 1993, 34, 3755; S. Kobayashi, I. Hachiya, T. Takahori, M. Araki and H. Ishitani, Tetrahedron Lett., 1992, 33, 6825.
10. For examples of lanthanide(III) catalysed Diels-Alder reactions in aqueous media, see K. Mikami, O. Kotera, Y. Motoyama and H. Sakaguchi, Synlett, 1995, 975; H. Sasai, T. Suzuki, N. Itoh, K. Tanaka, T. Date, K. Okamura and M. Shibazaki, Tetrahedron Lett., 1993, 34, 851; L. Yu, D. Chen and P. G. Wang, Tetrahedron Lett., 1996, 37, 2169; S. Kobayashi, I. Hachiya, M. Araki and H. Ishitani, Tetrahedron Lett., 1993, 34, 3755; S. Kobayashi, I. Hachiya, T. Takahori, M. Araki and H. Ishitani, Tetrahedron Lett., 1992, 33, 6825.
11. For examples of lanthanide(III) catalysed Diels-Alder reactions in aqueous media, see K. Mikami, O. Kotera, Y. Motoyama and H. Sakaguchi, Synlett, 1995, 975; H. Sasai, T. Suzuki, N. Itoh, K. Tanaka, T. Date, K. Okamura and M. Shibazaki, Tetrahedron Lett., 1993, 34, 851; L. Yu, D. Chen and P. G. Wang, Tetrahedron Lett., 1996, 37, 2169; S. Kobayashi, I. Hachiya, M. Araki and H. Ishitani, Tetrahedron Lett., 1993, 34, 3755; S. Kobayashi, I. Hachiya, T. Takahori, M. Araki and H. Ishitani, Tetrahedron Lett., 1992, 33, 6825.
12. For examples of lanthanide(III) catalysed Diels-Alder reactions in aqueous media, see K. Mikami, O. Kotera, Y. Motoyama and H. Sakaguchi, Synlett, 1995, 975; H. Sasai, T. Suzuki, N. Itoh, K. Tanaka, T. Date, K. Okamura and M. Shibazaki, Tetrahedron Lett., 1993, 34, 851; L. Yu, D. Chen and P. G. Wang, Tetrahedron Lett., 1996, 37, 2169; S. Kobayashi, I. Hachiya, M. Araki and H. Ishitani, Tetrahedron Lett., 1993, 34, 3755; S. Kobayashi, I. Hachiya, T. Takahori, M. Araki and H. Ishitani, Tetrahedron Lett., 1992, 33, 6825.
13. 3 is an excellent catalyst for the Mukaiyama aldol reaction in water, see T.-P. Loh, J. Pei and G.-Q. Cao, Chem. Commun., 1996, 1819.
14. The endo : exo ratio of the product is known to vary according to the concentration of the dienophile, see J. A. Berson, Z. Hamlet and W. A. Mueller, J. Am. Chem. Soc., 1962, 84, 297; R. Breslow, U. Maitra and D. Rideout, Tetrahedron Lett., 1983, 24, 1901; A. A.-Z. Samii, A. deSavignac, I. Rico and A. Lattes, Tetrahedron, 1985, 41, 3683.
15. The endo : exo ratio of the product is known to vary according to the concentration of the dienophile, see J. A. Berson, Z. Hamlet and W. A. Mueller, J. Am. Chem. Soc., 1962, 84, 297; R. Breslow, U. Maitra and D. Rideout, Tetrahedron Lett., 1983, 24, 1901; A. A.-Z. Samii, A. deSavignac, I. Rico and A. Lattes, Tetrahedron, 1985, 41, 3683.
16. The endo : exo ratio of the product is known to vary according to the concentration of the dienophile, see J. A. Berson, Z. Hamlet and W. A. Mueller, J. Am. Chem. Soc., 1962, 84, 297; R. Breslow, U. Maitra and D. Rideout, Tetrahedron Lett., 1983, 24, 1901; A. A.-Z. Samii, A. deSavignac, I. Rico and A. Lattes, Tetrahedron, 1985, 41, 3683.
17. D. A. Evans, K. T. Chapman and J. Bisaha, J. Am. Chem. Soc., 1988, 110, 1238 and references cited therein. Experimental detail will be reported in due course.