A novel synthetic method of bicyclic pyrans via the palladium-catalyzed tandem cyclization/ring expansion between enynals and dimethyl acetylenedicarboxylate

Synthesis

Volumn , Issue 9, 2004, Pages 1409-1412

  Sato, Kenichiro ^a   Yudha S , Salprima ^a   Asao, Naoki ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Bicyclic pyran; Cyclization; Palladium catalyst; Ring expansion; Tandem reaction

Indexed keywords

ACETYLATION; PALLADIUM; REACTION KINETICS;

BICYCLIC PYRANS; ENYNALS;

SYNTHESIS (CHEMICAL);

ACETYLENEDICARBOXYLIC ACID DIMETHYL ESTER; ALKADIENE; PALLADIUM; PALLADIUM ACETATE; PYRAN DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CYCLIZATION; SYNTHESIS;

EID: 3042750611     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-822361     Document Type: Article

References (6)

1. For reviews, see: (a) Kantorowski, E. J.; Kurth, M. J. Tetrahedron 2000, 56, 4317. (b) Roxburgh, C. J. Tetrahedron 1993, 47, 10749.
2. For reviews, see: (a) Kantorowski, E. J.; Kurth, M. J. Tetrahedron 2000, 56, 4317. (b) Roxburgh, C. J. Tetrahedron 1993, 47, 10749.
3. Asao, N.; Nogami, T.; Lee, S.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 10921.
4. (a) Asao, N.; Nogami, T.; Takahashi, K.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 764.
5. (b) Mondal, S.; Nogami, T.; Asao, N.; Yamamoto, Y. J. Org. Chem. 2003, 68, 9496.
6. Although we attempted to observe the formation of 6 in the reaction of Ia with Pd catalyst in the absence of 2, we could not detect it, probably due to very low stability of 6 under the reaction conditions mentioned above.