Remarkable regio-controlled effect of 1,3-diene as a ligand on nickel-promoted cyclization

Tetrahedron Letters

Volumn 37, Issue 6, 1996, Pages 887-890

  Sato, Yoshihiro ^a   Takimoto, Masanori ^a   Mori, Miwako ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; CYCLOPENTANE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030027784     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02291-0     Document Type: Article

References (16)

1. For reviews, see: (a) Jolly, P. W. In Comprehensive Organometallic Chemistry; Wilkinson, G.; Stone, F. G A.; Abel, E. W., Eds.; Pergamon: New York, 1982; Vol. 8, p 613. (b) Keim, W.; Behr, A.; Roper, M. ibid. p 371. (c) Heimback, P. Angew Chem., Int. Ed. Engl. 1973, 12, 975. (d) Wilke, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 185.
2. For reviews, see: (a) Jolly, P. W. In Comprehensive Organometallic Chemistry; Wilkinson, G.; Stone, F. G A.; Abel, E. W., Eds.; Pergamon: New York, 1982; Vol. 8, p 613. (b) Keim, W.; Behr, A.; Roper, M. ibid. p 371. (c) Heimback, P. Angew Chem., Int. Ed. Engl. 1973, 12, 975. (d) Wilke, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 185.
3. For reviews, see: (a) Jolly, P. W. In Comprehensive Organometallic Chemistry; Wilkinson, G.; Stone, F. G A.; Abel, E. W., Eds.; Pergamon: New York, 1982; Vol. 8, p 613. (b) Keim, W.; Behr, A.; Roper, M. ibid. p 371. (c) Heimback, P. Angew Chem., Int. Ed. Engl. 1973, 12, 975. (d) Wilke, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 185.
4. For reviews, see: (a) Jolly, P. W. In Comprehensive Organometallic Chemistry; Wilkinson, G.; Stone, F. G A.; Abel, E. W., Eds.; Pergamon: New York, 1982; Vol. 8, p 613. (b) Keim, W.; Behr, A.; Roper, M. ibid. p 371. (c) Heimback, P. Angew Chem., Int. Ed. Engl. 1973, 12, 975. (d) Wilke, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 185.
5. (a) For [4+4] cycloadditions, see: Wender, P. A.; Tebbe, M. J. Synthesis 1991, 1089 and references cited therein.
6. (b) Tamao, K.; Kobayashi, K.; Ito, Y. Syn. Lett. 1992, 539. Tamao, K.; Kobayashi, K.; Ito, Y. J. Synth. Org. Chem. Jpn. 1990, 48, 381.
7. (b) Tamao, K.; Kobayashi, K.; Ito, Y. Syn. Lett. 1992, 539. Tamao, K.; Kobayashi, K.; Ito, Y. J. Synth. Org. Chem. Jpn. 1990, 48, 381.
8. (c) For [4+2] cycloadditions, see: Wender, P. A.; Smith, T E. J. Org. Chem. 1995, 60, 2962 and referencees cited therein.
9. (d) For nickel-promoted intermolecular reactions of 1,3-diene and carbonyl compound, see: Baker, R.; Cook, A. H.; Crimmin, M. J. J. Chem. Soc. Chem. Commun. 1975, 727. Baker, R.; Crimmin, M. J. J. Chem. Soc. Perkin I 1979, 1264.
10. (d) For nickel-promoted intermolecular reactions of 1,3-diene and carbonyl compound, see: Baker, R.; Cook, A. H.; Crimmin, M. J. J. Chem. Soc. Chem. Commun. 1975, 727. Baker, R.; Crimmin, M. J. J. Chem. Soc. Perkin I 1979, 1264.
11. Sato, Y.; Takimoto, M.; Hayashi, K.; Katsuhara, T.; Takagi, K.; Mori, M. J. Am. Chem. Soc. 1994, 116, 9771.
12. For the synthesis of 1a, see: Müller, G.; Jas, G. Tetrahedron Lett. 1992, 33, 4417.
13. 2O provided no product containing deuterium. This result indicates that no C-Ni bond is formed at the last stage of this cyclization.
14. When 5′-I was treated with the hydride nickel complex 9 (30 mol %), no 5′-T was obtained and 5′-I was recovered in 90%. This indicates that olefin isomerization of 5′-I into 5′-T by nickel complex 9 does not occur. Scheme 4 formula presented
15. Halterman, R. L.; Vollhardt, K. P. C. Tetrahedron Lett. 1986, 27, 1461.
16. In this reaction, unchanged 22 was recovered in 69%, which indicates that diene 22 does not react with hydride nickel complex 4 under the conditions of this cyclization, and that 22 plays a role as a ligand to affect the reaction course.