The Diels-Alder reaction of phenylsulfonylacetylene and furan derivatives. Normal vs. Tandem 'pincer' reactions

Heterocycles

Volumn 50, Issue 2, 1999, Pages 653-656

  Arjona, Odón ^a   Iradier, Fátima ^a   Medel, Rocío ^a   Plumet, Joaquín ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; BENZENESULFONIC ACID DERIVATIVE; FURAN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; SYNTHESIS;

EID: 0033117423     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-98-s(h)85     Document Type: Article

References (12)

1. For recent reviews, see: a) S. Woo and B. A. Keay, Synthesis, 1996, 669.
2. b) P. Chiu and M. Lautens, Topics in Current Chemistry, 1997, 190, 3. For an excellent review on the furan Diels-Alder chemistry, see: C. O. Kappe, S. S. Murphree, and A. Padwa, Tetrahedron, 1997, 53, 14179.
3. b) P. Chiu and M. Lautens, Topics in Current Chemistry, 1997, 190, 3. For an excellent review on the furan Diels-Alder chemistry, see: C. O. Kappe, S. S. Murphree, and A. Padwa, Tetrahedron, 1997, 53, 14179.
4. J. L. Aceña, O. Arjona, and J. Plumet, J. Org. Chem., 1997, 62, 3360 and references therein.
5. For a study of the scope and limitations of this method, see: O. Arjona, R. Fernández de la Pradilla, A. de Dios, J. Plumet, and A. Viso, J. Org. Chem., 1994, 59, 3906.
6. For more recent applications, see: a) J. L. Aceña, O. Arjona, F. Iradier, and J. Plumet, Tetrahedron Lett., 1996, 37, 105.
7. b) J. L. Aceña, O. Arjona, M. L. León, and J. Plumet, Tetrahedron Lett., 1996, 37, 8975.
8. T. G. Back, S. Collins, and R. G. Kerr, J. Org. Chem., 1983, 48, 3077.
9. 13C) using selective decoupling and nOe1d experiments. All compounds give satisfactory analytical and spectroscopical data according to the proposed structures. Full details will be published elsewhere.
10. The tandem 'pincer' Diels-Alder reaction consist in "two consecutive Diels-Alder cycloadditions between two dienes and an acetylenic dienophile, which acts as a bis-dienophile". For a recent account on the synthetic use of this process, see: M. Lautens and E. Fillion, J. Org. Chem., 1997, 62, 4418.
11. In the case of furan (21), the reaction with 1 gave 71 % of the Michael adduct (22).
12. (formula presented) 21 22