Carbocyclization reaction of active methine compounds with unactivated alkenyl or alkynyl groups mediated by TiCl4-Et3N

Journal of Organic Chemistry

Volumn 63, Issue 25, 1998, Pages 9470-9475

  Kitagawa, Osamu ^a   Suzuki, Takashi ^a   Inoue, Tadashi ^a   Watanabe, Yoko ^a   Taguchi, Takeo ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL GROUP; ALKYNYL GROUP; CHLORIDE; CYCLOPENTANE DERIVATIVE; IODINE; TITANIUM;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CYCLIZATION; MOLECULAR DYNAMICS; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; TECHNIQUE;

EID: 0032509412     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981603k     Document Type: Article

References (35)

1. Examples of intramolecular carbometalation reactions of enolates with unactivated olefins or alkynes: (a) Fournet, G.; Balme, G.; Gore, J. Tetrahedron 1990, 46, 7763-7773. (b) Fournet, G.; Balme, G.; Gore, J. Tetrahedron 1991, 47, 6293-6304. (c) Yeh, M.-C. P.; Chuang, L.-W.; Ueng, C. H. J. Org. Chem. 1996, 61, 3874-3877. (d) Nakamura, E.; Sakata, G.; Kubota, K. Tetrahedron Lett. 1998, 39, 2157-2158. (e) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Manna, F.; Pace, P. Synlett 1998, 446-448. (f) Lorthiois, E.; Marek, I.; Normant, J. F. J. Org. Chem. 1998, 63, 2442-2450 and references therein.
2. Examples of intramolecular carbometalation reactions of enolates with unactivated olefins or alkynes: (a) Fournet, G.; Balme, G.; Gore, J. Tetrahedron 1990, 46, 7763-7773. (b) Fournet, G.; Balme, G.; Gore, J. Tetrahedron 1991, 47, 6293-6304. (c) Yeh, M.-C. P.; Chuang, L.-W.; Ueng, C. H. J. Org. Chem. 1996, 61, 3874-3877. (d) Nakamura, E.; Sakata, G.; Kubota, K. Tetrahedron Lett. 1998, 39, 2157-2158. (e) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Manna, F.; Pace, P. Synlett 1998, 446-448. (f) Lorthiois, E.; Marek, I.; Normant, J. F. J. Org. Chem. 1998, 63, 2442-2450 and references therein.
3. Examples of intramolecular carbometalation reactions of enolates with unactivated olefins or alkynes: (a) Fournet, G.; Balme, G.; Gore, J. Tetrahedron 1990, 46, 7763-7773. (b) Fournet, G.; Balme, G.; Gore, J. Tetrahedron 1991, 47, 6293-6304. (c) Yeh, M.-C. P.; Chuang, L.-W.; Ueng, C. H. J. Org. Chem. 1996, 61, 3874-3877. (d) Nakamura, E.; Sakata, G.; Kubota, K. Tetrahedron Lett. 1998, 39, 2157-2158. (e) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Manna, F.; Pace, P. Synlett 1998, 446-448. (f) Lorthiois, E.; Marek, I.; Normant, J. F. J. Org. Chem. 1998, 63, 2442-2450 and references therein.
4. Examples of intramolecular carbometalation reactions of enolates with unactivated olefins or alkynes: (a) Fournet, G.; Balme, G.; Gore, J. Tetrahedron 1990, 46, 7763-7773. (b) Fournet, G.; Balme, G.; Gore, J. Tetrahedron 1991, 47, 6293-6304. (c) Yeh, M.-C. P.; Chuang, L.-W.; Ueng, C. H. J. Org. Chem. 1996, 61, 3874-3877. (d) Nakamura, E.; Sakata, G.; Kubota, K. Tetrahedron Lett. 1998, 39, 2157-2158. (e) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Manna, F.; Pace, P. Synlett 1998, 446-448. (f) Lorthiois, E.; Marek, I.; Normant, J. F. J. Org. Chem. 1998, 63, 2442-2450 and references therein.
5. Examples of intramolecular carbometalation reactions of enolates with unactivated olefins or alkynes: (a) Fournet, G.; Balme, G.; Gore, J. Tetrahedron 1990, 46, 7763-7773. (b) Fournet, G.; Balme, G.; Gore, J. Tetrahedron 1991, 47, 6293-6304. (c) Yeh, M.-C. P.; Chuang, L.-W.; Ueng, C. H. J. Org. Chem. 1996, 61, 3874-3877. (d) Nakamura, E.; Sakata, G.; Kubota, K. Tetrahedron Lett. 1998, 39, 2157-2158. (e) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Manna, F.; Pace, P. Synlett 1998, 446-448. (f) Lorthiois, E.; Marek, I.; Normant, J. F. J. Org. Chem. 1998, 63, 2442-2450 and references therein.
6. Examples of intramolecular carbometalation reactions of enolates with unactivated olefins or alkynes: (a) Fournet, G.; Balme, G.; Gore, J. Tetrahedron 1990, 46, 7763-7773. (b) Fournet, G.; Balme, G.; Gore, J. Tetrahedron 1991, 47, 6293-6304. (c) Yeh, M.-C. P.; Chuang, L.-W.; Ueng, C. H. J. Org. Chem. 1996, 61, 3874-3877. (d) Nakamura, E.; Sakata, G.; Kubota, K. Tetrahedron Lett. 1998, 39, 2157-2158. (e) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Manna, F.; Pace, P. Synlett 1998, 446-448. (f) Lorthiois, E.; Marek, I.; Normant, J. F. J. Org. Chem. 1998, 63, 2442-2450 and references therein.
7. Examples of intermolecular carbometalation reactions of enolates to unactivated olefins or alkynes: (a) Bertrand, M. T.; Courtois, G.; Miginiac, L. Tetrahedron Lett. 1974, 1945-1948. (b) Ehrhardt, H.; Mildenberger, H. Liebigs Ann. Chem. 1982, 989-993. (c) Stack, J. G.; Simpson, R. D.; Hollander, F. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1990, 112, 2716-2729. (d) Yamaguchi, M.; Hayashi, A.; Hirama, M. J. Am. Chem. Soc. 1993, 115, 3362-3363. (e) Yamaguchi, M.; Hayashi, A.; Hirama, M. J. Synth. Chem. Org. Jpn. 1996, 54, 267-279. (f) Kubota, K.; Nakamura, E. Angew. Chem., Int. Ed. Engl. 1997, 36, 2491-2493.
8. Examples of intermolecular carbometalation reactions of enolates to unactivated olefins or alkynes: (a) Bertrand, M. T.; Courtois, G.; Miginiac, L. Tetrahedron Lett. 1974, 1945-1948. (b) Ehrhardt, H.; Mildenberger, H. Liebigs Ann. Chem. 1982, 989-993. (c) Stack, J. G.; Simpson, R. D.; Hollander, F. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1990, 112, 2716-2729. (d) Yamaguchi, M.; Hayashi, A.; Hirama, M. J. Am. Chem. Soc. 1993, 115, 3362-3363. (e) Yamaguchi, M.; Hayashi, A.; Hirama, M. J. Synth. Chem. Org. Jpn. 1996, 54, 267-279. (f) Kubota, K.; Nakamura, E. Angew. Chem., Int. Ed. Engl. 1997, 36, 2491-2493.
9. Examples of intermolecular carbometalation reactions of enolates to unactivated olefins or alkynes: (a) Bertrand, M. T.; Courtois, G.; Miginiac, L. Tetrahedron Lett. 1974, 1945-1948. (b) Ehrhardt, H.; Mildenberger, H. Liebigs Ann. Chem. 1982, 989-993. (c) Stack, J. G.; Simpson, R. D.; Hollander, F. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1990, 112, 2716-2729. (d) Yamaguchi, M.; Hayashi, A.; Hirama, M. J. Am. Chem. Soc. 1993, 115, 3362-3363. (e) Yamaguchi, M.; Hayashi, A.; Hirama, M. J. Synth. Chem. Org. Jpn. 1996, 54, 267-279. (f) Kubota, K.; Nakamura, E. Angew. Chem., Int. Ed. Engl. 1997, 36, 2491-2493.
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27. In the lactonization of 2b, when simply heating 2b as in the case of 2a, a chemical yield of 3b was low due to the formation of 1b. Thus, in this case, the lactonization through alkaline hydrolysis of the ester group was performed.
28. The stereochemistries of iodides 2c and 2d were determined on the basis of the lactonization experiment in accordance with Scheme 4.
29. The stereochemistries of 2g and 4k were determined on the basis of NOE experiments.
30. 2 to the C-C triple bond as a byproduct. On the other hand, the effect of temperature on the reaction pathways should be noted; that is, when the reaction of 1g was performed at room temperature, (E)- and (Z)-2g were obtained in a ratio of E/Z = 4/7 in 78% yield due to a competition of both iodocarbocylization and carbotitanation-iodonolysis processes.
31. 3N.
32. 3N to 1 equiv of the substrates resulted in a considerable decrease in the chemical yield due to the formation of unidentified byproducts.
33. 2 was added to the reaction solution.
34. 1b
35. Monteiro, N.; Gore, J.; Balme, G. Tetrahedron 1992, 48, 10103-10114.