Intramolecular carbostannation reaction of active methine compounds having an allenyl group mediated by SnCl4-Et3N

Tetrahedron Letters

Volumn 40, Issue 13, 1999, Pages 2549-2552

  Kitagawa, Osamu ^a   Suzuki, Takashi ^a   Fujiwara, Hiroki ^a   Taguchi, Takeo ^a  

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

Author keywords

Allenes; Cyclization; Cycloalkenes; Tin and compounds

Indexed keywords

ALLENE DERIVATIVE; CYCLOHEXANE; CYCLOPENTENE DERIVATIVE; METAL DERIVATIVE; STANNOUS CHLORIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONFORMATION; CONFORMATIONAL TRANSITION; CYCLIZATION; REACTION ANALYSIS; REACTION TIME; STEREOCHEMISTRY;

EID: 0033605868     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00199-9     Document Type: Article

References (25)

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17. (a) Kitagawa, O.; Suzuki, T.; Inoue, T.; Taguchi, T. Tetrahedron Lett. 1998, 39, 7357-7360.
18. (b) Kitagawa, O.; Suzuki, T.; Inoue, T.; Watanabe, Y.; Taguchi, T. J. Org. Chem. 1998, 63, 9470-9475.
19. Examples of carbostannation of Sn-enolate to alkynyl tin. (a) Yamaguchi, M.; Hayashi, A.; Hirama, M. J. Am. Chem. Soc. 1993, 115, 3362-3363.
20. (b) Yamaguchi, M.; Hayashi, A.; Hirama, M. J. Syn. Org. Chem. Jpn. 1996, 54, 267-279.
21. 3) δ: 170.9, 135.8, 131.5, 57.4, 53.0, 30.6, 25.5, 18.3, 7.3.
22. Sn-C = 41 Hz), 18.2.
23. Ma, S.; Negishi, E. J. Am. Chem. Soc. 1995, 117, 6345-6357.
24. The resulting intermediate 1A may be more stabilized in comparison with 1A′ due to the intramolecular coordination of two ester groups to the Sn atom.
25. Allenylated active methine compounds 1 were prepared according to reported procedures. Bates, R. W.; Rama-Devi, T.; Ko, H. Tetrahedron, 1995, 51, 12939-12954.