Reactions of acceptor thiophene 1,1-dioxides with dienes. Synthesis of bisadducts

Russian Chemical Bulletin

Volumn 54, Issue 9, 2005, Pages 2182-2186

  Nenajdenko, V G ^a   Moiseev, A M ^a   Balenkova, E S ^a  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

Acceptor thiophene 1,1 dioxides; Bisadduct; Diels Alder reaction; Dienes; Dienophile; Regioselectivity; Stereoselectivity

Indexed keywords

EID: 33645315486     PISSN: 10665285     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11172-006-0094-5     Document Type: Article

References (19)

1. J. Nakayama, R. Hasemi, K. Yoshimura, Y. Sugihara, S. Yamaoka, and N. Nakamura, J. Org. Chem., 1998, 63, 4912.
2. A. Tsirk, S. Gronowitz, and A.-B. Hoernfeldt, Acta Chem. Scand., B, 1998, 52, 533.
3. M. S. Raasch, J. Org. Chem., 1980, 45, 856.
4. J. Nakayama, Bull. Soc. Chem. Jpn, 2000, 73, 1.
5. V. G. Nenajdenko, A. E. Gavryushin, and E. S. Balenkova, Tetrahedron Lett., 2001, 42, 4397;
6. V. G. Nenajdenko, A. M. Moiseev, and E. S. Balenkova, Izv. Akad. Nauk, Ser. Khim., 2004, 2144
7. [Russ. Chem. Bull., Int. Ed., 2004, 53, 2241].
8. A. M. Moiseev, V. G. Nenajdenko, and E. S. Balenkova, Tetrahedron, 2005, 61, 10880.
9. O. Diels and K. Alder, Chem. Ber., 1929, 62, 2337.
10. D. W. Cameron, R. L. Evans, G. I. Feutrill, V. A. Patrick, B. W. Skelton, and A. H. White, Aust. J. Chem., 2003, 56, 1215.
11. W. Dmowski, V. A. Manko, and I. Nowak, J. Fluor. Chem., 1998, 88, 143.
12. D. Craig, J. Am. Chem. Soc., 1950, 72, 1678.
13. A. S. Onishchenko, Dienovyi Sintez [Diene Synthesis], Izd-vo Akad. Nauk SSSR, Moscow, 1963, 650 pp. (in Russian).
14. A. I. Konovalov and V. D. Kiselev, Izv. Akad. Nauk, Ser. Khim., 2003, 279
15. [Russ. Chem. Bull., Int. Ed., 2003, 52, 293].
16. F. Fringuelli and A. Taticchi, The Diels-Alder Reaction: Selected Practical Methods, Wiley, New York, 2002, 340 pp.
17. N. S. Simpkins, Sulphones in Organic Synthesis, Pergamon Press, Oxford, 1993, 381 pp.
18. E. J. Bush, D. W. Jones, and M. Thornton-Pett, Tetrahedron Lett., 1994, 52, 9755;
19. G. Sauer, U. Eder, G. Haffer, G. Neef, R. Wiechert, and G.-A. Hoyer, Liebigs Ann. Chem., 1982, 3, 448.