"Formal" ruthenium-catalyzed [4+2+2] cycloaddition of 1,6-diynes to 1,3-dienes: Formation of cyclooctatrienes vs vinylcyclohexadienes

Organic Letters

Volumn 5, Issue 16, 2003, Pages 2841-2844

  Varela, Jesús A ^a   Castedo, Luis ^a   Saá, Carlos ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; RUTHENIUM; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CONJUGATION; CYCLOADDITION; STEREOCHEMISTRY;

EID: 0141520554     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0348710     Document Type: Article

References (35)

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28. (i) For an excellent review on Ru-catalyzed C-C formation, see: Trost, B. M.; Dean Toste, F.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067. (ii) For Ru-catalyzed [2+2+2] cycloadditions, see: (a) Yamamoto, Y.; Takagishi, H.; Itoh, K. J. Am. Chem. Soc. 2002, 124, 28 and 6844. (b) Yamamoto, Y.; Ogawa, R.; Itoh, K. J. Am. Chem. Soc. 2001, 123, 6189. (c) Yamamoto, Y.; Takagishi, H.; Itoh, K. Org. Lett. 2001, 3, 2117. (d) Yamamoto, Y.; Okuda, S.; Itoh, K. Chem. Commun. 2000, 1102. (e) Yamamoto, Y.; Ogawa, R.; Itoh, K. Chem. Commun. 2000, 549. (f) Yamamoto, Y.; Kitahara, H.; Ogawa, R.; Itoh, K. J. Org. Chem. 1998, 63, 9610.
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31. The expected 1,3-cyclohexadienes have been observed in Ru-catalyzed [2+2+2] cycloaddition of 1,6-diynes to cyclic allyl ethers (ref 12f). However, when acyclic allyl ethers are used, regioisomeric 1,3-cyclohexadienes (analogues of 4) are obtained in good yield, a result attributed to the expected [2+2+2] cycloaddition being accompanied by a 1,5-H shift.
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33. Minor amounts of dimers and trimers of 1a are also obtained when using either of the two catalysts.
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35. Other conditions gave lower yields: rt, 21%; slow addition of 1a (2 h), rt, 47%; slow addition of 1a (4 h), rt, 58%. Dimers of 1a have also been observed in variable amounts.