Methylenecyclopentane annulation via formal [3+2] cycloaddition reaction

Tetrahedron Letters

Volumn 37, Issue 33, 1996, Pages 5943-5946

  Takahashi, Yoshinori ^a   Tanino, Keiji ^a   Kuwajima, Isao ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE;

ARTICLE; CYCLIZATION; MOLECULAR INTERACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030581417     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01283-X     Document Type: Article

References (10)

1. 1. (a) Ho, T.-L. Carbocycle Construction in Terpene Synthesis; VCH Publishers: New York, 1988.
2. (b) Hudlicky, T.; Rulin, F.; Lovelace, T. C.; Reed, J. W. in Studies in Natural Products Chemistry; Rahman, A., Ed.; ELSEVIER: Amsterdam, 1989; Vol. 3, pp 3-72.
3. 2. Hudlicky, T.; Price, J. D. Chem. Rev. 1989, 89, 1467-1486.
4. 3. (a) Little, R. D. in Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapter 3.1, pp 239-270.
5. (b) Chan, D. M. T. in Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapter 3.2, pp 271-314.
6. 4. Masuya, K.; Domon, K.; Tanino, K.; Kuwajima, I. Synlett, 1996, 157-158.
7. 5. Although this type of transformation has been achieved by palladium catalyzed annulation of 2-(acetoxymethyl)allyltrimethylsilane with electron-deficient olefins, it should be noted that the reaction is not applicable to electron-rich ones: Trost, B. Angew. Chem. Int. Ed. Engl. 1986, 25, 1-20.
8. 6. Fleming, I.; Dunoguès, J.; Smithers, R. Org. React. 1989, 37, 57-575.
9. 7. (a) Brückner, R. in Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 6, Chapter 4.6, pp 873-908.
10. (b) Nakai, T.; Mikami, K. Org. React. 1994, 46, 105-209.