Palladium-catalyzed cascade ring expansion reaction of 1-(3-methoxycarbonyloxy-1-propynyl)cyclobutanols with phenols

Tetrahedron Letters

Volumn 40, Issue 49, 1999, Pages 8583-8586

  Yoshida, Masahiro ^a   Nemoto, Hideo ^a,b   Ihara, Masataka ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b UNIVERSITY OF TOYAMA   (Japan)

Author keywords

Cyclopentanones; Palladium; Palladium compounds; Rearrangements; Ring transformations

Indexed keywords

ALCOHOL DERIVATIVE; CYCLOPENTANONE DERIVATIVE; PALLADIUM; PHENOL DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; REACTION ANALYSIS;

EID: 0033521042     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01749-9     Document Type: Article

References (17)

1. For our previous works on the palladium catalyzed ring expansion of cyclobutanols, see: (a) Nemoto, H.; Shiraki, M.; Fukumoto, K. Synlett 1994, 599-600.
2. (b) Nemoto, H.; Miyata, J.; Fukumoto, K. Tetrahedron 1996, 52, 10363-10374.
3. (c) Nemoto, H.; Miyata, J.; Yoshida, M.; Raku, N.; Fukumoto, K. J. Org. Chem. 1997, 62, 7850-7857.
4. Recently, Uemura et al. reported a palladium(II)-catalyzed oxidative ring cleavage reaction of cyclobutanols: Nishimura, T.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 1999, 121, 2645-2646.
5. For the application to natural product synthesis, see: (a) Nemoto, H.; Nagamochi, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1993, 2329-2332.
6. (b) Nemoto, H.; Nagamochi, M.; Ishibashi, H.; Fukumoto, K. J. Org. Chem. 1994, 59, 74-79.
7. (c) Nemoto, H.; Yoshida, M.; Fukumoto, K.; Ihara, M. Tetrahedron Lett. 1999, 40, 907-910.
8. (d) Nemoto, H.; Miyata, J.; Ihara, M. Tetrahedron Lett. 1999, 40, 1933-1936.
9. Nemoto, H.; Yoshida, M.; Fukumoto, K. J. Org. Chem. 1997, 62, 6450-6451.
10. For review, see: Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2589-2612, and references cited therein.
11. (a) Tsuji, J.; Watanabe, I.; Minami, I.; Shimizu, I. J. Am. Chem. Soc. 1985, 107, 2196-2198.
12. (b) Minami, I.; Yuhara, M.; Watanabe, H.; Tsuji, J. J. Organomet. Chem. 1987, 334, 225.
13. (c) Greeves, N.; Torode, J. S. Synthesis 1993, 1109.
14. (d) Geng, L.; Lu, X. Tetrahedron Lett. 1990, 31, 111-114.
15. (e) Minami, I.; Yuhara, Y; Tsuji, J. Tetrahedron Lett. 1987, 28, 629-632.
16. +-28), found: 254.1563.
17. +), found: 314.2232.