Stereoselectivity in intramolecular cyclization of non-conjugated unsaturated ketones by electroreduction

Chemistry Letters

Volumn , Issue 12, 2002, Pages 1254-1255

  Nishiguchi, Ikuzo ^a   Goda, Satoshi ^a   Yamada, Kouji ^a   Yamamoto, Yoshimasa ^a   Maekawa, Hirofumi ^a  

^a NAGAOKA UNIVERSITY OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; NITROGEN; SULFUR;

ARTICLE; CHEMICAL PARAMETERS; CONJUGATION; CYCLIZATION; EXPERIMENTATION; REDUCTION; STEREOCHEMISTRY;

EID: 0037028354     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2002.1254     Document Type: Article

References (13)

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2. b) T. Shono, I. Nishiguchi, H. Ohmizu, and M. Mitani, J. Am. Chem. Soc., 100, 545 (1978).
3. a) J. E. Swartz, T. J. Mahachi, and E. Kariv-Miller, J. Am. Chem. Soc., 110, 3622 (1988).
4. b) J. E. Swartz, E. Kariv-Miller, and S. J. Harrold, J. Am. Chem. Soc., 111, 1211 (1989).
5. c) F. Lombardo, R. A. Newmark, and E. Kariv-Miller, J. Org. Chem., 56, 2411 (1991).
6. d) S. Kashimura, M. Ishifune, Y. Murai, N. Moriyoshi, and T. Shono, Tetrahedron Lett., 36, 5029 (1980).
7. For electroreductive intramolecular cyclization between a keto group and an acetylenic or an allenic bond, see: a) T. Shono, I. Nishiguchi, and H. Ohmizu, Chem. Lett., 1976, 1233.
8. b) G. Pattenden and G. M. Robertson, Tetrahedron Lett., 24, 4617 (1983).
9. For electroreductive intramolecular coupling of an ester with an alkene, see: S. Kashimura, Y. Murai, M. Ishifune, M. Masuda, M. Shinomura, H. Murase, and T. Shono, Acta Chem. Scand., 53, 949 (1999).
10. B, Elsevier, Amsterdam (1985), pp 1-68.
11. The similar electroreduction of nitrogen-containing non-conjugated enone (2) using various metals other than A1 as the electrodes was found to give the product (5) in the following yields: Carbon (8%), Zn (7%), Sus (0%), and Pt (0%).
12. 13C NMR, IR, MASS) and elemental analysis.
13. "Kagaku Binran (Chemical Encyclopedia)," 4th ed., Basic Ver. II, ed. by The Chemical Society of Japan, Maruzen, Tokyo (1993), pp 622-655.