Enol ester as an olefinic partner in enyne cyclization. A novel tandem cyclization to stereodefined bicyclo[3.3.0]octenes

Journal of the American Chemical Society

Volumn 125, Issue 14, 2003, Pages 4036-4037

  Urabe, Hirokazu ^a   Suzuki, Daisuke ^a   Sasaki, Misa ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BICYCLO COMPOUND; BICYCLO[3.3.0]OCTENE; ESTER DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLIZATION; GEOMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0242417583     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja034369a     Document Type: Article

References (31)

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17. For recent alternatives of this method in the group 4 metal-mediated diene, enyne, or diyne cyclizations to give five-membered rings, see: Urabe, H.; Suzuki, K.; Sato, F. J. Am. Chem. Soc. 1997, 119, 10014-10027. Urabe, H.; Narita, M.; Sato, F. Angew. Chem., Int. Ed. 1999, 38, 3516-3518. Liu, Y.; Shen, B.; Kotora, M.; Takahashi, T. Angew. Chem., Int. Ed. 1999, 38, 949-951. Xi, C.; Kotora, M.; Nakajima, K.; Takahashi, T. J. Org. Chem. 2000, 65, 945-950. Xi, Z.; Li, P. Angew. Chem., Int. Ed. 2000, 39, 2950-2952.
18. For recent alternatives of this method in the group 4 metal-mediated diene, enyne, or diyne cyclizations to give five-membered rings, see: Urabe, H.; Suzuki, K.; Sato, F. J. Am. Chem. Soc. 1997, 119, 10014-10027. Urabe, H.; Narita, M.; Sato, F. Angew. Chem., Int. Ed. 1999, 38, 3516-3518. Liu, Y.; Shen, B.; Kotora, M.; Takahashi, T. Angew. Chem., Int. Ed. 1999, 38, 949-951. Xi, C.; Kotora, M.; Nakajima, K.; Takahashi, T. J. Org. Chem. 2000, 65, 945-950. Xi, Z.; Li, P. Angew. Chem., Int. Ed. 2000, 39, 2950-2952.
19. For recent alternatives of this method in the group 4 metal-mediated diene, enyne, or diyne cyclizations to give five-membered rings, see: Urabe, H.; Suzuki, K.; Sato, F. J. Am. Chem. Soc. 1997, 119, 10014-10027. Urabe, H.; Narita, M.; Sato, F. Angew. Chem., Int. Ed. 1999, 38, 3516-3518. Liu, Y.; Shen, B.; Kotora, M.; Takahashi, T. Angew. Chem., Int. Ed. 1999, 38, 949-951. Xi, C.; Kotora, M.; Nakajima, K.; Takahashi, T. J. Org. Chem. 2000, 65, 945-950. Xi, Z.; Li, P. Angew. Chem., Int. Ed. 2000, 39, 2950-2952.
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22. For details, see the Supporting Information.
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27. To the best of our knowledge, enol esters have not been investigated for olefin-olefin or -acetylene coupling reactions mediated by group 4 metal reagents.
28. For the generation and reactions of stereodefined metalacycles from (E) or (Z)-olefinic substrates, see: Negishi, E.; Choueiry, D.; Nguyen, T. B.; Swanson, D. R. J. Am. Chem. Soc. 1994, 116, 9751-9752. Narita, M.;: Urabe, H.; Sato, F. Angew. Chem., Int. Ed. 2002, 41, 3671-3674 and references therein. For the configurational stability of α-acyloxy organotitanium compounds, see: Hoppe, D.; Krämer, T. Angew. Chem., Int. Ed. Engl. 1986, 25, 160-162. Zschage, O.; Hoppe, D. Tetrahedron 1992, 48, 5657-5666.
29. For the generation and reactions of stereodefined metalacycles from (E) or (Z)-olefinic substrates, see: Negishi, E.; Choueiry, D.; Nguyen, T. B.; Swanson, D. R. J. Am. Chem. Soc. 1994, 116, 9751-9752. Narita, M.;: Urabe, H.; Sato, F. Angew. Chem., Int. Ed. 2002, 41, 3671-3674 and references therein. For the configurational stability of α-acyloxy organotitanium compounds, see: Hoppe, D.; Krämer, T. Angew. Chem., Int. Ed. Engl. 1986, 25, 160-162. Zschage, O.; Hoppe, D. Tetrahedron 1992, 48, 5657-5666.
30. For the generation and reactions of stereodefined metalacycles from (E) or (Z)-olefinic substrates, see: Negishi, E.; Choueiry, D.; Nguyen, T. B.; Swanson, D. R. J. Am. Chem. Soc. 1994, 116, 9751-9752. Narita, M.;: Urabe, H.; Sato, F. Angew. Chem., Int. Ed. 2002, 41, 3671-3674 and references therein. For the configurational stability of α-acyloxy organotitanium compounds, see: Hoppe, D.; Krämer, T. Angew. Chem., Int. Ed. Engl. 1986, 25, 160-162. Zschage, O.; Hoppe, D. Tetrahedron 1992, 48, 5657-5666.
31. For the generation and reactions of stereodefined metalacycles from (E) or (Z)-olefinic substrates, see: Negishi, E.; Choueiry, D.; Nguyen, T. B.; Swanson, D. R. J. Am. Chem. Soc. 1994, 116, 9751-9752. Narita, M.;: Urabe, H.; Sato, F. Angew. Chem., Int. Ed. 2002, 41, 3671-3674 and references therein. For the configurational stability of α-acyloxy organotitanium compounds, see: Hoppe, D.; Krämer, T. Angew. Chem., Int. Ed. Engl. 1986, 25, 160-162. Zschage, O.; Hoppe, D. Tetrahedron 1992, 48, 5657-5666.