Pd-catalyzed ring opening of cyclopropanols

Synlett

Volumn , Issue 5, 2000, Pages 629-630

  Okumoto, Hiroshi ^a   Jinnai, Takamitsu ^a   Shimizu, Hiroyuki ^a   Harada, Yoshinori ^a   Mishima, Hideki ^a   Suzuki, Akira ^a  

^a KURASHIKI UNIVERSITY OF SCIENCE AND THE ARTS   (Japan)

Author keywords

Catalysis; Cyclopropanol; Dehydrogenations; Enone; Palladium

Indexed keywords

PALLADIUM; PROPANOL;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; HYDROGENATION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0034128012     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (10)

1. Ito, Y.; Fujii, S.; Saegusa, T. J. Org. Chem. 1976, 41, 2073. Kirihara, M.; Ichinose, M.; Takizawa, S.; Momose, T. Chem. Commun. 1998, 1691. Blake, A. J.; Highton, A. J.; Majid, T. N.; Simpkins, N. S. Org. Lett. 1999, I, 1787, and references cited therein.
2. Ito, Y.; Fujii, S.; Saegusa, T. J. Org. Chem. 1976, 41, 2073. Kirihara, M.; Ichinose, M.; Takizawa, S.; Momose, T. Chem. Commun. 1998, 1691. Blake, A. J.; Highton, A. J.; Majid, T. N.; Simpkins, N. S. Org. Lett. 1999, I, 1787, and references cited therein.
3. Ito, Y.; Fujii, S.; Saegusa, T. J. Org. Chem. 1976, 41, 2073. Kirihara, M.; Ichinose, M.; Takizawa, S.; Momose, T. Chem. Commun. 1998, 1691. Blake, A. J.; Highton, A. J.; Majid, T. N.; Simpkins, N. S. Org. Lett. 1999, I, 1787, and references cited therein.
4. Park, S.; Cha, J. K. Org. Lett. 2000, 2, 147.
5. Kulinkovich, O. G.; Sviridov, S. V.; Vasilevski, D. A. Synthesis 1991, 234.
6. Actually, a small amount of acid such as CSA effected the reaction to give only 3a in 64% yield. Similar conversion is described. Mizojiri, R.; Urabe, H.; Sato, F. Tetrahedron Lett. 1999, 40, 2557. Lee, K.; Kim, S.; Cha, J. K. J. Org. Chem. 1998, 63, 9135.
7. Actually, a small amount of acid such as CSA effected the reaction to give only 3a in 64% yield. Similar conversion is described. Mizojiri, R.; Urabe, H.; Sato, F. Tetrahedron Lett. 1999, 40, 2557. Lee, K.; Kim, S.; Cha, J. K. J. Org. Chem. 1998, 63, 9135.
8. During our investigation, a similar ring opening reaction of cyclobutanol derivatives appeared, in which Pd(II) reagent was used in pyridine under oxygen atmosphere. The conditions were applied to 1a, however, no remarkable improvement was obtained. Nishimura, T.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 1999, 121, 2645.
9. 2 (0.05 mmol) in MeCN (5 ml) was stirred at 50 °C for ca. 20h. The reaction mixture was passed through a short florisil column with AcOEt and the filtrates were concentrated. The residue was concentrated and chromatographed to obtain the enone 2.
10. Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158.