Cycloisomerization of 1,6-enynes: Asymmetric multistep preparation of a hydrindane framework in water with polymeric catalysts

Organic Letters

Volumn 7, Issue 2, 2005, Pages 291-293

  Nakai, Yasushi ^a   Uozumi, Yasuhiro ^a  

^a GRADUATE UNIVERSITY FOR ADVANCED STUDIES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; COPOLYMER; CYCLOPENTANE DERIVATIVE; PALLADIUM COMPLEX; POLYMER; RESIN; WATER;

ALKYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; ISOMERIZATION; SYNTHESIS;

EID: 13444278828     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047700j     Document Type: Article

References (37)

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11. For reviews on heterogeneous-switching, see: (a) Bailey, D. C.; Langer, S. H. Chem. Rev. 1981, 81, 109. (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217. (c) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035. (d) Dörwald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, 2000. (e) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217. (f) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275. (g) De Vos, D. E., Vankelecom, I. F. J., Jacobs, P. A., Eds. Chiral Catalyst Immobilization and Recycling; Wiley-VCH: Weinheim, 2000. (h) Fan, Q.-H.; Li, Y.-M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385.
12. For reviews on heterogeneous-switching, see: (a) Bailey, D. C.; Langer, S. H. Chem. Rev. 1981, 81, 109. (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217. (c) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035. (d) Dörwald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, 2000. (e) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217. (f) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275. (g) De Vos, D. E., Vankelecom, I. F. J., Jacobs, P. A., Eds. Chiral Catalyst Immobilization and Recycling; Wiley-VCH: Weinheim, 2000. (h) Fan, Q.-H.; Li, Y.-M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385.
13. For reviews on heterogeneous-switching, see: (a) Bailey, D. C.; Langer, S. H. Chem. Rev. 1981, 81, 109. (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217. (c) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035. (d) Dörwald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, 2000. (e) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217. (f) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275. (g) De Vos, D. E., Vankelecom, I. F. J., Jacobs, P. A., Eds. Chiral Catalyst Immobilization and Recycling; Wiley-VCH: Weinheim, 2000. (h) Fan, Q.-H.; Li, Y.-M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385.
14. For reviews on heterogeneous-switching, see: (a) Bailey, D. C.; Langer, S. H. Chem. Rev. 1981, 81, 109. (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217. (c) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035. (d) Dörwald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, 2000. (e) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217. (f) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275. (g) De Vos, D. E., Vankelecom, I. F. J., Jacobs, P. A., Eds. Chiral Catalyst Immobilization and Recycling; Wiley-VCH: Weinheim, 2000. (h) Fan, Q.-H.; Li, Y.-M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385.
15. For reviews on heterogeneous-switching, see: (a) Bailey, D. C.; Langer, S. H. Chem. Rev. 1981, 81, 109. (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217. (c) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035. (d) Dörwald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, 2000. (e) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217. (f) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275. (g) De Vos, D. E., Vankelecom, I. F. J., Jacobs, P. A., Eds. Chiral Catalyst Immobilization and Recycling; Wiley-VCH: Weinheim, 2000. (h) Fan, Q.-H.; Li, Y.-M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385.
16. For studies on polymer-supported palladium catalysts reported by the author's group, see: (a) Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1997, 38, 3557. (b) Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341. (c) Uozumi, Y.; Danjo, H.; Hayashi, T. J. Org. Chem. 1999, 64, 3384. (d) Uozumi, Y.; Watanabe, T. J. Org. Chem. 1999, 64, 6921. (e) Uozumi, Y.; Nakai, Y. Org. Lett. 2002, 4, 2997. (f) Uozumi, Y.; Kimura, T. Synlett 2002, 2045. (g) Hocke, H.; Uozumi, Y. Synlett 2002, 2049. (h) Uozumi, Y.; Kobayashi, Y. Heterocycles 2003, 59, 71. (i) Uozumi, Y.; Nakao, R. Angew. Chem., Int. Ed. 2003, 42, 194.
17. For studies on polymer-supported palladium catalysts reported by the author's group, see: (a) Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1997, 38, 3557. (b) Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341. (c) Uozumi, Y.; Danjo, H.; Hayashi, T. J. Org. Chem. 1999, 64, 3384. (d) Uozumi, Y.; Watanabe, T. J. Org. Chem. 1999, 64, 6921. (e) Uozumi, Y.; Nakai, Y. Org. Lett. 2002, 4, 2997. (f) Uozumi, Y.; Kimura, T. Synlett 2002, 2045. (g) Hocke, H.; Uozumi, Y. Synlett 2002, 2049. (h) Uozumi, Y.; Kobayashi, Y. Heterocycles 2003, 59, 71. (i) Uozumi, Y.; Nakao, R. Angew. Chem., Int. Ed. 2003, 42, 194.
18. For studies on polymer-supported palladium catalysts reported by the author's group, see: (a) Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1997, 38, 3557. (b) Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341. (c) Uozumi, Y.; Danjo, H.; Hayashi, T. J. Org. Chem. 1999, 64, 3384. (d) Uozumi, Y.; Watanabe, T. J. Org. Chem. 1999, 64, 6921. (e) Uozumi, Y.; Nakai, Y. Org. Lett. 2002, 4, 2997. (f) Uozumi, Y.; Kimura, T. Synlett 2002, 2045. (g) Hocke, H.; Uozumi, Y. Synlett 2002, 2049. (h) Uozumi, Y.; Kobayashi, Y. Heterocycles 2003, 59, 71. (i) Uozumi, Y.; Nakao, R. Angew. Chem., Int. Ed. 2003, 42, 194.
19. For studies on polymer-supported palladium catalysts reported by the author's group, see: (a) Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1997, 38, 3557. (b) Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341. (c) Uozumi, Y.; Danjo, H.; Hayashi, T. J. Org. Chem. 1999, 64, 3384. (d) Uozumi, Y.; Watanabe, T. J. Org. Chem. 1999, 64, 6921. (e) Uozumi, Y.; Nakai, Y. Org. Lett. 2002, 4, 2997. (f) Uozumi, Y.; Kimura, T. Synlett 2002, 2045. (g) Hocke, H.; Uozumi, Y. Synlett 2002, 2049. (h) Uozumi, Y.; Kobayashi, Y. Heterocycles 2003, 59, 71. (i) Uozumi, Y.; Nakao, R. Angew. Chem., Int. Ed. 2003, 42, 194.
20. For studies on polymer-supported palladium catalysts reported by the author's group, see: (a) Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1997, 38, 3557. (b) Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341. (c) Uozumi, Y.; Danjo, H.; Hayashi, T. J. Org. Chem. 1999, 64, 3384. (d) Uozumi, Y.; Watanabe, T. J. Org. Chem. 1999, 64, 6921. (e) Uozumi, Y.; Nakai, Y. Org. Lett. 2002, 4, 2997. (f) Uozumi, Y.; Kimura, T. Synlett 2002, 2045. (g) Hocke, H.; Uozumi, Y. Synlett 2002, 2049. (h) Uozumi, Y.; Kobayashi, Y. Heterocycles 2003, 59, 71. (i) Uozumi, Y.; Nakao, R. Angew. Chem., Int. Ed. 2003, 42, 194.
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