Intramolecular cyclizations of enynes using RuClH(CO)(PPh3)3

Journal of Organic Chemistry

Volumn 63, Issue 25, 1998, Pages 9158-9159

  Nishida, Mayumi ^a   Adachi, Naoko ^a   Onozuka, Kiyoko ^a   Matsumura, Hiroshi ^a   Mori, Miwako ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALKYNE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0032509411     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981715b     Document Type: Article

References (18)

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6. Levison J. J.; Robinson. S. D. J. Chem. Soc. A 1970, 2947.
7. Trost reported that the same type of compound as I was obtained in the Pd-catalyzed enyne cyclization. Trost, B. M.; Romero, D. L.; Rise, L. J. Am. Chem. Soc. 1994, 116, 4268.
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12. (e) Hirai, K.; Matunaga, T. Organometallics 1994, 13, 1878.
13. 2 = COOEt) as substrates. In the case of 1f and 1g, double-bond isomerization took place to provide deconjugated compounds. In the reaction of 1h, the starting material was recovered. Unfortunately, a six-membered ring compound was not formed in the reaction of (E)-9-(4-methoxyphenyl)-2-nonen-7-ynote.
14. HMBC data of 5a indicated that the aromatic group was connected to the tertially vinyllic carbon.
15. 2 = Et) as the substrates. In the reaction of 3e, the starting material was recovered. In the case of 3g, double-bond isomerization took place to provide deconjugated compounds. However, in the reaction of 3f, a cyclized product was obtained in 22% yield along with 15% of 3f.
16. (a) Blackmore, T.; Bruce, M. I.; Stone, F. G. A. J. Chem. Soc., Dalton Trans. 1974, 106.
17. (b) Hart, D. W.; Schwartz, J. J. Organomet. Chem. 1975, 87, C11.
18. Since the same tendency in the effects of substituents on the aromatic ring was shown in each reaction (Tables 1 and 2), the rate-determining step would be irreversible intramolecular olefin insertion. An electron-withdrawing group on alkyne stabilized the produced vinylruthenium complex through back-donation, which retarded olefin insertion.