Rhodium(I)-catalyzed intramolecular hydroacylation of 4,6-dienals: Novel synthesis of cycloheptenones

Synthesis

Volumn , Issue 15, 2007, Pages 2323-2336

  Oonishi, Yoshihiro ^a   Mori, Miwako ^b   Sato, Yoshihiro ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b HEALTH SCIENCES UNIVERSITY OF HOKKAIDO   (Japan)

Author keywords

Cyclization; Dienals; Hydroacylation; Rhodium; Transition metals

Indexed keywords

CYCLOHEPTENONES; E-OLEFIN; INTRAMOLECULAR HYDROACYLATION; OLEFINIC GEOMETRY;

ACYLATION; AROMATIC COMPOUNDS; CATALYSIS; CYCLIZATION; OLEFINS; SUBSTITUTION REACTIONS;

RHODIUM COMPOUNDS;

1 [(2 HYDROXYETHOXY)METHYL] 6 (PHENYLTHIO)THYMINE; 2 (1 METHYL 3 PHENYLPROPYLIDENE)CYCLOPENTANONE; 2 (2 CYCLOHEXYLETHYL)CYCLOHEPT 2 ENONE; 2 (4 CYCLOHEXYLBUTYLIDENE)CYCLOPENTANONE; 2 (4 PHENYLBUT 1 ENYL)CYCLOPENTANONE; 2 (4 PHENYLBUTYLIDENE)CYCLOPENTANONE; 2 [3 (BENZYLOXY)PROPYLIDENE]CYCLOPENTANONE; 2 ETHYLIDENECYCLOPENTANONE; 2 ETHYLIDENEOCTAHYDROINDEN 1 ONE; 2 PHENETHYLCYCLOHEPT 3 ENONE; 2 PROPYLIDENEOCTAHYDROINDEN 1 ONE; 4,6 DIENAL DERIVATIVE; ALKADIENE; ALKENE; CYCLOHEPTENONE; CYCLOPENTANONE DERIVATIVE; DICHLOROETHANE; INDENE DERIVATIVE; RHODIUM; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CARBONYLATION; CATALYSIS; COLUMN CHROMATOGRAPHY; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; ISOMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 34547797949     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-983774     Document Type: Article

References (36)

1. For reviews, see: (a) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635; and references cited therein.
2. (b) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49; and references cited therein.
3. (c) Trost, B. M. Science 1991, 254, 1471; and references cited therein.
4. (d) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259; and references cited therein.
5. Sakai, K.; Ide, J.; Oda, O.; Nakamura, N. Tetrahedron Lett. 1972, 1287.
6. (a) Lochow, C. F.; Miller, R. G. J. Am. Chem. Soc. 1976, 98, 1281.
7. (b) Larock, R. C.; Oertle, K.; Potter, G. F. J. Am. Chem. Soc. 1980, 102, 190.
8. (c) Sakai, K.; Ishiguro, Y.; Funakoshi, K.; Ueno, K.; Suemune, H. Tetrahedron Lett. 1984, 25, 961.
9. (d) Fairlie, D. P.; Bosnich, B. Organometallics 1988, 7, 936.
10. (a) James, B. R.; Young, C. G. J. Chem. Soc., Chem. Commun. 1983, 1215.
11. (b) James, B. R.; Young, C. G. J. Organomet. Chem. 1985, 285, 321.
12. (c) Taura, Y.; Tanaka, M.; Funakoshi, K.; Sakai, K. Tetrahedron Lett. 1989, 30, 6349.
13. (d) Tanaka, M.; Imai, M.; Fujio, M.; Sakamoto, E.; Takahashi, M.; Eto-Kato, Y.; Wu, X. M.; Funakoshi, K.; Sakai, K.; Suemune, H. J. Org. Chem. 2000, 65, 5806.
14. (e) Tanaka, M.; Sakai, K.; Suemune, H. Curr. Org. Chem. 2003, 7, 353.
15. (f) Barnhart, R. W.; Wang, X.; Noheda, P.; Bergens, S. H.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1994, 116, 1821.
16. (g) Bosnich, B. Acc. Chem. Res. 1998, 31, 667.
17. (h) Kundu, K.; McCullagh, J. V.; Morehead, A. T. Jr. J. Am. Chem. Soc. 2005, 127, 16042; and references cited therein.
18. Gable, K. P.; Benz, G. A. Tetrahedron Lett. 1991, 32, 3473.
19. Aloise, A. D.; Layton, M. E.; Shair, M. D. J. Am. Chem. Soc. 2000, 122, 12610.
20. Bendorf, H. D.; Colella, C. M.; Dixon, E. C.; Marchetti, M.; Matukonis, A. N.; Musselman, J. D.; Tiley, T. A. Tetrahedron Lett. 2002, 43, 7031.
21. Takeishi, K.; Sugishima, K.; Sasaki, K.; Tanaka, K. Chem. Eur. J. 2004, 10, 5681.
22. Portions of this work have previously been communicated, see: Sato, Y.; Oonishi, Y.; Mori, M. Angew. Chem. Int. Ed. 2002, 41, 1218.
23. Moxham, G. L.; Randell-Sly, H. E.; Brayshaw, S. K.; Woodward, R. L.; Weller, A. S.; Willis, M. C. Angew. Chem. Int. Ed. 2006, 45, 7618.
24. Spino, C.; Crawford, J.; Bishop, J. J. Org. Chem. 1995, 60, 844.
25. Barrow, R. A.; Hemscheidt, T.; Paik, L. S.; Moore, R. E.; Tius, M. A. J. Am. Chem. Soc. 1995, 117, 2479.
26. Kang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049.
27. Iseki, K.; Shinoda, M.; Ishiyama, C.; Hayashi, Y.; Shibasaki, M. Chem. Lett. 1986, 559.
28. Hong, S.; Kawaoka, A. M.; Mark, T. J. J. Am. Chem. Soc. 2003, 125, 15878.
29. Menzel, K.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 3718.
30. Abiru, T.; Miyashita, T.; Watanabe, Y.; Yamaguchi, T.; Machida, H.; Matsuda, A. J. Med. Chem. 1992, 35, 2253.
31. Matikainen, J.; Kaltia, S.; Hase, T. Tetrahedron 1993, 49, 8007.
32. Mann, S.; Carillon, S.; Breyne, O.; Marquet, A. Chem. Eur. J. 2002, 8, 439.
33. Harrowven, D. C.; May, P. J.; Bradley, M. Tetrahedron Lett. 2003, 44, 503.
34. Betancort, J. M.; Martín, V. S.; Padrón, J. M.; Palazón, J. M.; Ramírez, M. A.; Soler, M. A. J. Org. Chem. 1997, 62, 4570.
35. Paquette, L. A.; Crouse, G. D.; Sharma, A. K. J. Am. Chem. Soc. 1982, 104, 4411.
36. Arnecke, R.; Groth, U.; Köhler, T. Liebigs Ann. Chem. 1994, 891.