One-pot synthesis of a variety of 1,4-alkadienes and 1,2,4-alkatrienes from alkynes, allyl, or propargyl compounds and electrophiles by a (η2- propene)Ti(O-i-Pr)2-mediated reaction

Synthesis

Volumn , Issue 7, 2000, Pages 975-979

  Okamoto, Sentaro ^a   Takayama, Yuuki ^a   Gao, Yuan ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

1,2,4 trienes; 1,4 dienes; Allenes; Coupling; Titanium

Indexed keywords

1,2,4 ALKATRIENE DERIVATIVE; 1,4 ALKADIENE DERIVATIVE; ALKADIENE; ALKYNE; ALLYL COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; COMPLEX FORMATION; JAPAN; MOLECULAR INTERACTION; SYNTHESIS;

EID: 0033948553     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6296     Document Type: Article

References (32)

1. For organometallic-based preparation of 1,4-dienes by coupling of vinyl and allyl groups, see: Lipshutz, B. H.; Elworthy, T. R. J. Org. Chem. 1990, 55, 1695; and references cited therein.
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3. Tang, J.; Okada, K.; Shinokubo, H.; Oshima, K, Tetrahedron 1997, 53, 5061. Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1999, 64, 4095; and references cited therein.
4. Oppolzer, W. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; pp 29-61.
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11. a) Takayama, Y.; Gao, Y.; Sato, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 851.
12. b) Takayama, Y.; Okamoto, S.; Sato, F. Tetrahedron Lett. 1997, 38, 8351.
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15. e) Takayama, Y.; Okamoto, S.; Sato, F. J. Am. Chem. Soc. 1999, 121, 3559.
16. A similar type of tantalum-mediated reaction was reported. Takai, K.; Yamada, M.; Odaka, H.; Utimoto, K.; Fujii, T.; Furukawa, I. Chem. Lett. 1995, 315; and references cited therein.
17. 2-butene)-mediated reaction of alkynes with alkenyl acetals providing the corresponding 1,4-alkadienes has been reported, see: ref. 4b and 4c.
18. 2-butene) was reported (ref. 4a-c); however, the reaction with aldehydes was not reported.
19. Denmark, S. E. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; pp 751-784. Yoshida, K.; Grieco, P. A. Chem. Lett. 1985, 155. Lopez, S.; Rodriguez, J.; Rey, J. G.; de Lera, A. R. J. Am. Chem Soc. 1996, 118, 1881. Murakami, M.; Ubukata, M.; Itami, K.; Ito, Y. Angew, Chem., Int. Ed. Engl. 1998, 37, 2248. Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1999, 121, 4130.
20. Denmark, S. E. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; pp 751-784. Yoshida, K.; Grieco, P. A. Chem. Lett. 1985, 155. Lopez, S.; Rodriguez, J.; Rey, J. G.; de Lera, A. R. J. Am. Chem Soc. 1996, 118, 1881. Murakami, M.; Ubukata, M.; Itami, K.; Ito, Y. Angew, Chem., Int. Ed. Engl. 1998, 37, 2248. Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1999, 121, 4130.
21. Denmark, S. E. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; pp 751-784. Yoshida, K.; Grieco, P. A. Chem. Lett. 1985, 155. Lopez, S.; Rodriguez, J.; Rey, J. G.; de Lera, A. R. J. Am. Chem Soc. 1996, 118, 1881. Murakami, M.; Ubukata, M.; Itami, K.; Ito, Y. Angew, Chem., Int. Ed. Engl. 1998, 37, 2248. Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1999, 121, 4130.
22. Denmark, S. E. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; pp 751-784. Yoshida, K.; Grieco, P. A. Chem. Lett. 1985, 155. Lopez, S.; Rodriguez, J.; Rey, J. G.; de Lera, A. R. J. Am. Chem Soc. 1996, 118, 1881. Murakami, M.; Ubukata, M.; Itami, K.; Ito, Y. Angew, Chem., Int. Ed. Engl. 1998, 37, 2248. Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1999, 121, 4130.
23. Denmark, S. E. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; pp 751-784. Yoshida, K.; Grieco, P. A. Chem. Lett. 1985, 155. Lopez, S.; Rodriguez, J.; Rey, J. G.; de Lera, A. R. J. Am. Chem Soc. 1996, 118, 1881. Murakami, M.; Ubukata, M.; Itami, K.; Ito, Y. Angew, Chem., Int. Ed. Engl. 1998, 37, 2248. Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1999, 121, 4130.
24. Knight, D. W. In Comprehensive Organic Synthesis, Vol. 3; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; pp 481-520. Brandsma, L.; Verkruijsse, H. D. Synthesis of Acetylenes, Allenes and Cumulenes, A Laboratry Manual; Elsevier: Amsterdam, 1981. Mandai, T.; Ogawa, M.; Yamaoki, H.; Nakata, T.; Murayama, H.; Kawada, M.; Tsuji, J. Tetrahedron Lett. 1991, 32, 3397. Tolstikov, G. A.; Romanova, T. Y.; Kuchin, A. V. J. Organomet. Chem. 1985, 255, 71. Ruitenberg, K.; Kleijn, H.; Elsevier, C. J.; Meijer, J.; Vermeer, P. Tetrahedron Lett. 1981, 22, 1451.
25. Knight, D. W. In Comprehensive Organic Synthesis, Vol. 3; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; pp 481-520. Brandsma, L.; Verkruijsse, H. D. Synthesis of Acetylenes, Allenes and Cumulenes, A Laboratry Manual; Elsevier: Amsterdam, 1981. Mandai, T.; Ogawa, M.; Yamaoki, H.; Nakata, T.; Murayama, H.; Kawada, M.; Tsuji, J. Tetrahedron Lett. 1991, 32, 3397. Tolstikov, G. A.; Romanova, T. Y.; Kuchin, A. V. J. Organomet. Chem. 1985, 255, 71. Ruitenberg, K.; Kleijn, H.; Elsevier, C. J.; Meijer, J.; Vermeer, P. Tetrahedron Lett. 1981, 22, 1451.
26. Knight, D. W. In Comprehensive Organic Synthesis, Vol. 3; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; pp 481-520. Brandsma, L.; Verkruijsse, H. D. Synthesis of Acetylenes, Allenes and Cumulenes, A Laboratry Manual; Elsevier: Amsterdam, 1981. Mandai, T.; Ogawa, M.; Yamaoki, H.; Nakata, T.; Murayama, H.; Kawada, M.; Tsuji, J. Tetrahedron Lett. 1991, 32, 3397. Tolstikov, G. A.; Romanova, T. Y.; Kuchin, A. V. J. Organomet. Chem. 1985, 255, 71. Ruitenberg, K.; Kleijn, H.; Elsevier, C. J.; Meijer, J.; Vermeer, P. Tetrahedron Lett. 1981, 22, 1451.
27. Knight, D. W. In Comprehensive Organic Synthesis, Vol. 3; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; pp 481-520. Brandsma, L.; Verkruijsse, H. D. Synthesis of Acetylenes, Allenes and Cumulenes, A Laboratry Manual; Elsevier: Amsterdam, 1981. Mandai, T.; Ogawa, M.; Yamaoki, H.; Nakata, T.; Murayama, H.; Kawada, M.; Tsuji, J. Tetrahedron Lett. 1991, 32, 3397. Tolstikov, G. A.; Romanova, T. Y.; Kuchin, A. V. J. Organomet. Chem. 1985, 255, 71. Ruitenberg, K.; Kleijn, H.; Elsevier, C. J.; Meijer, J.; Vermeer, P. Tetrahedron Lett. 1981, 22, 1451.
28. Knight, D. W. In Comprehensive Organic Synthesis, Vol. 3; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; pp 481-520. Brandsma, L.; Verkruijsse, H. D. Synthesis of Acetylenes, Allenes and Cumulenes, A Laboratry Manual; Elsevier: Amsterdam, 1981. Mandai, T.; Ogawa, M.; Yamaoki, H.; Nakata, T.; Murayama, H.; Kawada, M.; Tsuji, J. Tetrahedron Lett. 1991, 32, 3397. Tolstikov, G. A.; Romanova, T. Y.; Kuchin, A. V. J. Organomet. Chem. 1985, 255, 71. Ruitenberg, K.; Kleijn, H.; Elsevier, C. J.; Meijer, J.; Vermeer, P. Tetrahedron Lett. 1981, 22, 1451.
29. Metallo-ene or -yne allene reaction using allenyl zinc compounds has been reported, see: Meyer, C.; Marek, I.; Courtemanche, G.; Normant, J. F. J. Org. Chem. 1995, 60, 863. Courtemanche, G.; Normant, J. F. Tetrahedron Lett. 1991, 32, 5317. Meyer, C.; Marek, I.; Normant, J. F. Tetrahedron Lett. 1994, 35, 5645.
30. Metallo-ene or -yne allene reaction using allenyl zinc compounds has been reported, see: Meyer, C.; Marek, I.; Courtemanche, G.; Normant, J. F. J. Org. Chem. 1995, 60, 863. Courtemanche, G.; Normant, J. F. Tetrahedron Lett. 1991, 32, 5317. Meyer, C.; Marek, I.; Normant, J. F. Tetrahedron Lett. 1994, 35, 5645.
31. Metallo-ene or -yne allene reaction using allenyl zinc compounds has been reported, see: Meyer, C.; Marek, I.; Courtemanche, G.; Normant, J. F. J. Org. Chem. 1995, 60, 863. Courtemanche, G.; Normant, J. F. Tetrahedron Lett. 1991, 32, 5317. Meyer, C.; Marek, I.; Normant, J. F. Tetrahedron Lett. 1994, 35, 5645.
32. Allene formation by the reaction of olefins with propargyl silyl ethers mediated by a zirconocene complex has been reported. Takahashi, T.; Hara, R.; Huo, S.; Ura, Y. Leese, M. P.; Suzuki, N. Tetrahedron Lett, 1997, 38, 8723.