Stereo- and regioselective bromination of 1,5-cyclooctadiene derivatives and their substitution reactions with organocopper reagents

Synlett

Volumn , Issue 12, 1997, Pages 1393-1394

  Baba, Yoshiyasu ^a   Noutary, Carole ^a   Ichikawa, Satsuki ^a   Kusumoto, Tetsuo ^a   Watanabe, Hisayuki ^b   Adachi, Michiaki ^b   Hotta, Hiroyasu ^b   Nakajima, Yasuyuki ^b   Arai, Kazutaka ^b   Hiyama, Tamejiro ^c  

^a SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

^b NISSAN CHEMICAL INDUSTRIES LTD   (Japan)

^c TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0344771704     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1069     Document Type: Article

References (14)

1. Petasis, N. A.; Patane, M. A. Tetrahedron 1992, 48, 5757.
2. For previous synthetic efforts towards cyclooctanoid skeletons, see: (a) Still, W. C.; Galynker, I. Tetrahedron 1981, 37, 3981.
3. (b) Schreiber, S. L.; Smith, D. B.; Schulte, G. J. Org. Chem. 1989, 54, 5994.
4. Green, B.; Lahav, M.; Schmidt, M. J. Chem. Soc. (B) 1971, 1552.
5. Details will be reported elsewhere.
6. Cf. Oda, M.; Kawase, T.; Kurata, H. Organic Syntheses 1995, 73, 240. When 3 was irradiated in the presence of 1 mol equiv. of NBS, monobromide 8 was obtained in 59% yield, which also was a key intermediate for the substituted 1,5-cyclooctadiene-1,2,5,6-tetracarboxylates. Details of the reaction will be discussed in due course. (Matrix Presented)
7. ORTEP drawing of 4.
8. Lipshutz, B. H.; Wilhelm, R. S. J. Am. Chem. Soc. 1981, 103, 7672.
9. Posner, G. H. Organic Reactions 1975, 22, 253.
10. Yamamoto, Y. Angew. Chem. Int. Ed. Engl. 1986, 25, 947.
11. + +1), 445, 443, 363, 303.
12. 2-symmetric nature, which led us to conclude that the stereochemistry of 6 and 7 should be cis, but that of 5 remains yet to be studied.
13. Ibuka, T.; Minakata, H.; Mitsui, Y.; Kinoshita, K.; Kawai, Y. J. Chem. Soc.. Chem. Commun. 1980, 1193.
14. Watanabe, T.; Yasumoto, K.; Murata, M.; Tagawa, M.; Narushima, H.; Furusato, T.; Kuwahara, M.; Hanaue, M.; Seki, T. Jpn. Kokai Tokkyo Koho, 1994, JP 06-184157; EP 582267; US 5346919; Chem. Abstr. 1994, 121, 7432t.