Novel [3+2] annulation via a trimethylenemethane zwitterion equivalent in water

Tetrahedron Letters

Volumn 37, Issue 4, 1996, Pages 471-474

  Lu, Yue Qi ^a   Li, Chao Jun ^a  

^a Tulane University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030052781     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02201-5     Document Type: Article

References (34)

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2. For representative reviews, see: Paquette, L. A. Top. Curr. Chem. 1984, 119, 1; Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. For reviews, see: Trost, B. M. Angew. Chem. Int. Ed. Engl. 1986, 25, 1; Wojcicki, A. Coord. Chem. Rev. 1990, 105, 35; Rosenblum, M. J. Organomet. Chem. 1986, 300, 191; Herndon, J. W.; Wu, C.; Harp, J. J.; Kreuzer, K. A. Synlett 1991, 2, 1; Welker, M. E. Chem. Rev. 1992, 92, 97.
3. For representative reviews, see: Paquette, L. A. Top. Curr. Chem. 1984, 119, 1; Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. For reviews, see: Trost, B. M. Angew. Chem. Int. Ed. Engl. 1986, 25, 1; Wojcicki, A. Coord. Chem. Rev. 1990, 105, 35; Rosenblum, M. J. Organomet. Chem. 1986, 300, 191; Herndon, J. W.; Wu, C.; Harp, J. J.; Kreuzer, K. A. Synlett 1991, 2, 1; Welker, M. E. Chem. Rev. 1992, 92, 97.
4. For representative reviews, see: Paquette, L. A. Top. Curr. Chem. 1984, 119, 1; Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. For reviews, see: Trost, B. M. Angew. Chem. Int. Ed. Engl. 1986, 25, 1; Wojcicki, A. Coord. Chem. Rev. 1990, 105, 35; Rosenblum, M. J. Organomet. Chem. 1986, 300, 191; Herndon, J. W.; Wu, C.; Harp, J. J.; Kreuzer, K. A. Synlett 1991, 2, 1; Welker, M. E. Chem. Rev. 1992, 92, 97.
5. For representative reviews, see: Paquette, L. A. Top. Curr. Chem. 1984, 119, 1; Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. For reviews, see: Trost, B. M. Angew. Chem. Int. Ed. Engl. 1986, 25, 1; Wojcicki, A. Coord. Chem. Rev. 1990, 105, 35; Rosenblum, M. J. Organomet. Chem. 1986, 300, 191; Herndon, J. W.; Wu, C.; Harp, J. J.; Kreuzer, K. A. Synlett 1991, 2, 1; Welker, M. E. Chem. Rev. 1992, 92, 97.
6. For representative reviews, see: Paquette, L. A. Top. Curr. Chem. 1984, 119, 1; Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. For reviews, see: Trost, B. M. Angew. Chem. Int. Ed. Engl. 1986, 25, 1; Wojcicki, A. Coord. Chem. Rev. 1990, 105, 35; Rosenblum, M. J. Organomet. Chem. 1986, 300, 191; Herndon, J. W.; Wu, C.; Harp, J. J.; Kreuzer, K. A. Synlett 1991, 2, 1; Welker, M. E. Chem. Rev. 1992, 92, 97.
7. For representative reviews, see: Paquette, L. A. Top. Curr. Chem. 1984, 119, 1; Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. For reviews, see: Trost, B. M. Angew. Chem. Int. Ed. Engl. 1986, 25, 1; Wojcicki, A. Coord. Chem. Rev. 1990, 105, 35; Rosenblum, M. J. Organomet. Chem. 1986, 300, 191; Herndon, J. W.; Wu, C.; Harp, J. J.; Kreuzer, K. A. Synlett 1991, 2, 1; Welker, M. E. Chem. Rev. 1992, 92, 97.
8. For representative reviews, see: Paquette, L. A. Top. Curr. Chem. 1984, 119, 1; Trost, B. M. Chem. Soc. Rev. 1982, 11, 141. For reviews, see: Trost, B. M. Angew. Chem. Int. Ed. Engl. 1986, 25, 1; Wojcicki, A. Coord. Chem. Rev. 1990, 105, 35; Rosenblum, M. J. Organomet. Chem. 1986, 300, 191; Herndon, J. W.; Wu, C.; Harp, J. J.; Kreuzer, K. A. Synlett 1991, 2, 1; Welker, M. E. Chem. Rev. 1992, 92, 97.
9. For other examples of indium mediated reactions in aqueous media, see: Li, C. J. Tetrahedron Lett. 1995, 36, 17; Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7071; Chan, T. H.; Li, C. J. J. Chem. Soc., Chem. Commun. 1992, 747; Chan, T. H.; Lee, M. C. J. Org. Chem. 1995, 60, 4228; Chan, T. H.; ; Kalyanam, N; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1993, 58, 7937; Gao, J. ; Harter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714; Prenner, R. H.; Binder, W. H.; Schmid, W. Liebigs Ann. Chem. 1994, 73; Paquette, L. A.; Mitzel, T. M. Tetrahedron Lett. 1995, 36, 6863.
10. For other examples of indium mediated reactions in aqueous media, see: Li, C. J. Tetrahedron Lett. 1995, 36, 17; Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7071; Chan, T. H.; Li, C. J. J. Chem. Soc., Chem. Commun. 1992, 747; Chan, T. H.; Lee, M. C. J. Org. Chem. 1995, 60, 4228; Chan, T. H.; ; Kalyanam, N; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1993, 58, 7937; Gao, J. ; Harter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714; Prenner, R. H.; Binder, W. H.; Schmid, W. Liebigs Ann. Chem. 1994, 73; Paquette, L. A.; Mitzel, T. M. Tetrahedron Lett. 1995, 36, 6863.
11. For other examples of indium mediated reactions in aqueous media, see: Li, C. J. Tetrahedron Lett. 1995, 36, 17; Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7071; Chan, T. H.; Li, C. J. J. Chem. Soc., Chem. Commun. 1992, 747; Chan, T. H.; Lee, M. C. J. Org. Chem. 1995, 60, 4228; Chan, T. H.; ; Kalyanam, N; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1993, 58, 7937; Gao, J. ; Harter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714; Prenner, R. H.; Binder, W. H.; Schmid, W. Liebigs Ann. Chem. 1994, 73; Paquette, L. A.; Mitzel, T. M. Tetrahedron Lett. 1995, 36, 6863.
12. For other examples of indium mediated reactions in aqueous media, see: Li, C. J. Tetrahedron Lett. 1995, 36, 17; Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7071; Chan, T. H.; Li, C. J. J. Chem. Soc., Chem. Commun. 1992, 747; Chan, T. H.; Lee, M. C. J. Org. Chem. 1995, 60, 4228; Chan, T. H.; ; Kalyanam, N; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1993, 58, 7937; Gao, J. ; Harter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714; Prenner, R. H.; Binder, W. H.; Schmid, W. Liebigs Ann. Chem. 1994, 73; Paquette, L. A.; Mitzel, T. M. Tetrahedron Lett. 1995, 36, 6863.
13. For other examples of indium mediated reactions in aqueous media, see: Li, C. J. Tetrahedron Lett. 1995, 36, 17; Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7071; Chan, T. H.; Li, C. J. J. Chem. Soc., Chem. Commun. 1992, 747; Chan, T. H.; Lee, M. C. J. Org. Chem. 1995, 60, 4228; Chan, T. H.; ; Kalyanam, N; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1993, 58, 7937; Gao, J. ; Harter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714; Prenner, R. H.; Binder, W. H.; Schmid, W. Liebigs Ann. Chem. 1994, 73; Paquette, L. A.; Mitzel, T. M. Tetrahedron Lett. 1995, 36, 6863.
14. For other examples of indium mediated reactions in aqueous media, see: Li, C. J. Tetrahedron Lett. 1995, 36, 17; Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7071; Chan, T. H.; Li, C. J. J. Chem. Soc., Chem. Commun. 1992, 747; Chan, T. H.; Lee, M. C. J. Org. Chem. 1995, 60, 4228; Chan, T. H.; ; Kalyanam, N; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1993, 58, 7937; Gao, J. ; Harter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714; Prenner, R. H.; Binder, W. H.; Schmid, W. Liebigs Ann. Chem. 1994, 73; Paquette, L. A.; Mitzel, T. M. Tetrahedron Lett. 1995, 36, 6863.
15. For other examples of indium mediated reactions in aqueous media, see: Li, C. J. Tetrahedron Lett. 1995, 36, 17; Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7071; Chan, T. H.; Li, C. J. J. Chem. Soc., Chem. Commun. 1992, 747; Chan, T. H.; Lee, M. C. J. Org. Chem. 1995, 60, 4228; Chan, T. H.; ; Kalyanam, N; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1993, 58, 7937; Gao, J. ; Harter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714; Prenner, R. H.; Binder, W. H.; Schmid, W. Liebigs Ann. Chem. 1994, 73; Paquette, L. A.; Mitzel, T. M. Tetrahedron Lett. 1995, 36, 6863.
16. For other examples of indium mediated reactions in aqueous media, see: Li, C. J. Tetrahedron Lett. 1995, 36, 17; Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7071; Chan, T. H.; Li, C. J. J. Chem. Soc., Chem. Commun. 1992, 747; Chan, T. H.; Lee, M. C. J. Org. Chem. 1995, 60, 4228; Chan, T. H.; ; Kalyanam, N; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1993, 58, 7937; Gao, J. ; Harter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714; Prenner, R. H.; Binder, W. H.; Schmid, W. Liebigs Ann. Chem. 1994, 73; Paquette, L. A.; Mitzel, T. M. Tetrahedron Lett. 1995, 36, 6863.
17. For other examples of indium mediated reactions in aqueous media, see: Li, C. J. Tetrahedron Lett. 1995, 36, 17; Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7071; Chan, T. H.; Li, C. J. J. Chem. Soc., Chem. Commun. 1992, 747; Chan, T. H.; Lee, M. C. J. Org. Chem. 1995, 60, 4228; Chan, T. H.; ; Kalyanam, N; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1993, 58, 7937; Gao, J. ; Harter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714; Prenner, R. H.; Binder, W. H.; Schmid, W. Liebigs Ann. Chem. 1994, 73; Paquette, L. A.; Mitzel, T. M. Tetrahedron Lett. 1995, 36, 6863.
18. Li, C. J.; Lu, Y. Q. Tetrahedron Lett. 1995, 36, 2721.
19. For reviews about this reaction, see: Li, C. J. Chem. Rev. 1993, 93, 2023; Li, C. J. Tetrahedron, in press; T. H. Chan; C. J. Li.; M. C. Lee; Z. Y. Wei Can. J. Chem. 1994, 72, 1181; Chan, T. H. Pure Appl. Chem. 1995, 67, 0000 in press.
20. For reviews about this reaction, see: Li, C. J. Chem. Rev. 1993, 93, 2023; Li, C. J. Tetrahedron, in press; T. H. Chan; C. J. Li.; M. C. Lee; Z. Y. Wei Can. J. Chem. 1994, 72, 1181; Chan, T. H. Pure Appl. Chem. 1995, 67, 0000 in press.
21. For reviews about this reaction, see: Li, C. J. Chem. Rev. 1993, 93, 2023; Li, C. J. Tetrahedron, in press; T. H. Chan; C. J. Li.; M. C. Lee; Z. Y. Wei Can. J. Chem. 1994, 72, 1181; Chan, T. H. Pure Appl. Chem. 1995, 67, 0000 in press.
22. For reviews about this reaction, see: Li, C. J. Chem. Rev. 1993, 93, 2023; Li, C. J. Tetrahedron, in press; T. H. Chan; C. J. Li.; M. C. Lee; Z. Y. Wei Can. J. Chem. 1994, 72, 1181; Chan, T. H. Pure Appl. Chem. 1995, 67, 0000 in press.
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