Rh(I)-catalyzed intramolecular carbonylative [2+2+1] cycloaddition reaction: Preparation of bicyclo[5.3.0]decadienones with substituted cyclopentenone frameworks

Chemical and Pharmaceutical Bulletin

Volumn 62, Issue 1, 2014, Pages 84-87

  Mukai, Chisato ^a   Takahashi, Yasuhito ^a   Ogawa, Kumiko ^a   Hayashi, Yujiro ^a   Inagaki, Fuyuhiko ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

2+2+1 cycloaddition; Allene; Rhodium

Indexed keywords

ALLENE DERIVATIVE; CYCLOPENTENONE; TOLUENE;

ARTICLE; CARBONYLATION; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CONCEPTUAL FRAMEWORK; CYCLOADDITION; DIASTEREOISOMER; MELTING POINT; REACTION TIME; SUBSTITUTION REACTION; SYNTHESIS;

BICYCLO COMPOUNDS; CATALYSIS; CYCLIZATION; CYCLOADDITION REACTION; CYCLOPENTANES; RHODIUM;

EID: 84892186021     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.c13-00711     Document Type: Article

References (23)

1. Inagaki F., Kitagaki S., Mukai C., Synlett, 2011, 594-614 (2011).
2. Mukai C., Nomura I., Yamanishi K., Hanaoka M., Org. Lett., 4, 1755-1758 (2002).
3. Mukai C., Nomura I., Kitagaki S., J. Org. Chem., 68, 1376-1385 (2003).
4. Mukai C., Inagaki F., Yoshida T., Kitagaki S., Tetrahedron Lett., 45, 4117-4121 (2004).
5. Mukai C., Inagaki F., Yoshida T., Yoshitani K., Hara Y., Kitagaki S., J. Org. Chem., 70, 7159-7171 (2005).
6. Mukai C., Hirose T., Teramoto S., Kitagaki S., Tetrahedron, 61, 10983-10994 (2005).
7. Inagaki F., Mukai C., Org. Lett., 8, 1217-1220 (2006).
8. Inagaki F., Itoh N., Hayashi Y., Matsui Y., Mukai C., Beilstein J. Org. Chem., 7, 404-409 (2011).
9. Khand I. U., Knox G. R., Pauson P. L., Watts W. E., J. Chem. Soc. D, 36a (1971).
10. Khand I. U., Knox G. R., Pauson P. L., Watts W. E., Foreman M. I., J. Chem. Soc., Perkin Trans. 1, 1973, 977-981 (1973).
11. Geis O., Schmalz H.-G., Angew. Chem. Int. Ed., 37, 911-914 (1998).
12. Brummond K. M., Kent J. L., Tetrahedron, 56, 3263-3283 (2000).
13. Gibson S. E., Stevenazzi A., Angew. Chem. Int. Ed., 42, 1800-1810 (2003).
14. Blanco-Urgoiti J., Añorbe L., Pérez-Serrano L., Domínguez G., Pérez-Castells J., Chem. Soc. Rev., 33, 32-42 (2004).
15. Boñaga L. V. R., Krafft M. E., Tetrahedron, 60, 9795-9833 (2004).
16. Shibata T., Adv. Synth. Catal., 348, 2328-2336 (2006).
17. Mukai C., Sonobe H., Kim J. S., Hanaoka M., J. Org. Chem., 65, 6654-6659 (2000).
18. Inagaki F., Narita S., Hasegawa T., Kitagaki S., Mukai C., Angew. Chem. Int. Ed., 48, 2007-2011 (2009).
19. Kawamura T., Inagaki F., Narita S., Takahashi Y., Hirata S., Kitagaki S., Mukai C., Chemistry, 16, 5173-5183 (2010).
20. Shafawati M. T. S., Inagaki F., Kawamura T., Mukai C., Tetrahedron, 69, 1509-1515 (2013).
21. When we investigated the intramolecular PKTR of 1,1,3-trisubstituted allene-alkynes, a slimilar improvement of the chemical yield was observed with aid of increase CO pressure. See refs. 4 and 5.
22. The similar [2+2] cycloaddition of bis(allene)s leading to the formation of the bicyclo[5.2.0]nona-1,6-dienes was recorded. See refs. 18 and 19.
23. Synthetic procedure and characterization data of bis(allene)s 5 are summarized in Supplemental Information.