Stereoselective Iodocyclopropanation of Terminal Alkenes with Iodoform, Chromium(II) Chloride, and N,N,N′,N′-Tetraethylethylenediamine

Journal of the American Chemical Society

Volumn 125, Issue 43, 2003, Pages 12990-12991

  Takai, Kazuhiko ^a   Toshikawa, Shota ^a   Inoue, Atsushi ^a   Kokumai, Ryo ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CHROMIUM CHLORIDE; ETHYLENE DERIVATIVE; IODOFORM; N,N,N',N' TETRAETHYLETHYLENEDIAMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CYCLOPROPANATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0142245600     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0373061     Document Type: Article

References (29)

1. (a) Marek, I.; Normant, J. F. Chem. Rev. 1996, 96, 3241-3267. Knochel, P.; Normant, J. F. Tetrahedron Lett. 1986, 27, 1039-1042.
2. (a) Marek, I.; Normant, J. F. Chem. Rev. 1996, 96, 3241-3267. Knochel, P.; Normant, J. F. Tetrahedron Lett. 1986, 27, 1039-1042.
3. (b) Pine, S. H.; Zahler, R.; Evans, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 1980, 102, 3270-3272.
4. (c) Charette, A. B.; Gagnon, A.; Fournier, J. F. J. Am. Chem. Soc. 2002, 124, 386-387.
5. Takai, K.; Nitta, K.; Utimoto, K. J. Am. Chem. Soc. 1986, 108, 7408-7410.
6. Beckhaus, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 686-713.
7. For example, the Tebbe reagent reacts with olefins via a titanocene-methylene complex after treatment with DMAP. Lee, J. B.; Gajda, G. J.; Schaefer, W. P.; Howard, T. R.; Ikariya, T.; Straus, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 1981, 103, 7358-7361.
8. (a) Piers, E.; Coish, P. D. Synthesis 1995, 47-55. Moss, R. A.; Wilk, B. ; Krogh-Jespersen, K.; Westbrook, J. D. J. Am. Chem. Soc. 1989, 111, 6729-6734.
9. (a) Piers, E.; Coish, P. D. Synthesis 1995, 47-55. Moss, R. A.; Wilk, B. ; Krogh-Jespersen, K.; Westbrook, J. D. J. Am. Chem. Soc. 1989, 111, 6729-6734.
10. (b) Yachi, K.; Shinokubo, H.; Oshima, K. Angew. Chem., Int. Ed. 1998, 37, 2515-2517. See also ref 1c.
11. (c) Mathias, R.; Weyerstahl, P. Chem. Ber. 1979, 112, 3041-3053.
12. Yang, N. C.; Marolewski, T. A. J. Am. Chem. Soc. 1968, 90, 5644-5646. Nishimura, J.; Furukawa, J. Chem. Commun. 1971, 1375-1376. Miyano, S.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1974, 47, 1500-1503. Marolewski, T. A.; Yang, N. C. Org. Synth. 1988, Coll. Vol. 6, 974-975. Dehmlow, E. V.; Soufi, J.; Stammler, H.-G.; Neumann, B. Chem. Ber. 1993, 126, 499-502.
13. Yang, N. C.; Marolewski, T. A. J. Am. Chem. Soc. 1968, 90, 5644-5646. Nishimura, J.; Furukawa, J. Chem. Commun. 1971, 1375-1376. Miyano, S.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1974, 47, 1500-1503. Marolewski, T. A.; Yang, N. C. Org. Synth. 1988, Coll. Vol. 6, 974-975. Dehmlow, E. V.; Soufi, J.; Stammler, H.-G.; Neumann, B. Chem. Ber. 1993, 126, 499-502.
14. Yang, N. C.; Marolewski, T. A. J. Am. Chem. Soc. 1968, 90, 5644-5646. Nishimura, J.; Furukawa, J. Chem. Commun. 1971, 1375-1376. Miyano, S.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1974, 47, 1500-1503. Marolewski, T. A.; Yang, N. C. Org. Synth. 1988, Coll. Vol. 6, 974-975. Dehmlow, E. V.; Soufi, J.; Stammler, H.-G.; Neumann, B. Chem. Ber. 1993, 126, 499-502.
15. Yang, N. C.; Marolewski, T. A. J. Am. Chem. Soc. 1968, 90, 5644-5646. Nishimura, J.; Furukawa, J. Chem. Commun. 1971, 1375-1376. Miyano, S.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1974, 47, 1500-1503. Marolewski, T. A.; Yang, N. C. Org. Synth. 1988, Coll. Vol. 6, 974-975. Dehmlow, E. V.; Soufi, J.; Stammler, H.-G.; Neumann, B. Chem. Ber. 1993, 126, 499-502.
16. Yang, N. C.; Marolewski, T. A. J. Am. Chem. Soc. 1968, 90, 5644-5646. Nishimura, J.; Furukawa, J. Chem. Commun. 1971, 1375-1376. Miyano, S.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1974, 47, 1500-1503. Marolewski, T. A.; Yang, N. C. Org. Synth. 1988, Coll. Vol. 6, 974-975. Dehmlow, E. V.; Soufi, J.; Stammler, H.-G.; Neumann, B. Chem. Ber. 1993, 126, 499-502.
17. 2, 61% (82:18), 2,2′-bipyridyl, 13% (64:36).
18. Charette, A. B.; Beauchemin, A. Org. React. 2001, 58, 1-415.
19. 2 (4 equiv) resulted in iodoolefination, but the yield of 10 decreased to 54% (E:Z= 54:46), and 12 was recovered in 43% yield; 14 was not detected.
20. When 2-fold amounts of the reagent A were used, 16 was obtained in 13% yield (a diastereomeric mixture) along with 10 in 75% yield (E:Z= 54:46). (diagram presented)
21. The reactant 12 was recovered in 27% yield. The iodoolefins 10 and 16 were obtained as byproducts in 3% and 6% yields, respectively.
22. Dorwald, F. Z. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim, 1999; pp 105-119.
23. For the formation of cyclopropanes by reductive elimination of metallocyclobutanes, see: (a) Ti: Horikawa, Y.; Nomura, T.; Watanabe, M.; Fujiwara, T.; Takeda, T. J. Org. Chem. 1997, 62, 3678-3682.
24. (b) Re: Yang, G. K.; Bergman, R. G. Organometallics 1985, 4, 129-138.
25. 2 In contrast, when TMEDA (4 equiv) was added to the geminal dichromium reagent generated at 25°C for 1 h, and the mixture was stirred for a further 15 min, treatment of 12 with the new base-added reagent at 25°C for 2 h gave 14 in 38% yield (trans:cis = 80:20) along with 10 and 16 in I% and 3% yields, respectively. The reactant 12 was recovered in 37% yield.
26. A chromium-alkylidene complex having a TMEDA ligand was isolated, see: Hao, S.; Song, J.-I.; Berno, P.; Gambarotta, S. Organometallics 1994, 13, 1326-1335.
27. For a review, see: Donaldson, W. A. Tetrahedron 2001, 57, 8589-8627.
28. (a) Charette, A. B.; Giroux, A. J. Org. Chem. 1996, 61, 8718-8719.
29. (b) Charette, A. B.; De Freitas-Gil, R. P. Tetrahedron Lett. 1997, 38, 2809-2812.