Vinyl-allenes as dienes in the Lewis acid-mediated hetero Diels–Alder reaction with aldehydes

作者: David Regás , Marı́a M Afonso , Antonio Galindo , J.Antonio Palenzuela

DOI: 10.1016/S0040-4039(00)01140-0

关键词: AldehydeChemistryCycloadditionDiels–Alder reactionLewis acids and basesOrganic chemistry

摘要: Abstract The Lewis acid-mediated, hetero Diels–Alder reaction of a vinyl-allene system with aldehydes as heterodienophiles has been carried out. In the cases studied, only two cycloadducts have obtained, which correspond to endo (major compound) and exo (minor approach aldehyde through less hindered face dienic system.

参考文章(11)
M. Teresa Mujica, María M. Afonso, Antonio Galindo, J. Antonio Palenzuela, Enantioselective Synthesis of α,β,α‘-Trisubstituted Cyclic Ethers† Journal of Organic Chemistry. ,vol. 63, pp. 9728- 9738 ,(1998) , 10.1021/JO981188W
Claude Spino, Carl Thibault, Stéphane Gingras, Stereoselective Construction of Tetrasubstituted Exocyclic Alkenes from the [4 + 2]-Cycloaddition of Vinylallenes Journal of Organic Chemistry. ,vol. 63, pp. 5283- 5287 ,(1998) , 10.1021/JO980482L
William H. Okamura, Michael L. Curtin, Pericyclization of Vinylallenes in Organic Synthesis: On the Intramolecular Diels-Alder Reaction Synlett. ,vol. 1990, pp. 1- 9 ,(1990) , 10.1055/S-1990-20973
J. Antonio Palenzuela, Hassan Y. Elnagar, William H. Okamura, Selective cis-trans isomerization of a tetraene via an allene intermediate. Geometric isomerism via an sp2 to sp2 sigmatropic hydrogen shift and kinetic isotope effect studies Journal of the American Chemical Society. ,vol. 111, pp. 1770- 1773 ,(1989) , 10.1021/JA00187A032
Angel R. de Lera, Alicia Torrado, José García Rey, Susana López, Alkylidene-2H-pyrans by thermal electrocyclic ring closure of (2Z)-divinylallenals Tetrahedron Letters. ,vol. 38, pp. 7421- 7424 ,(1997) , 10.1016/S0040-4039(97)01746-2
Susana López, Jesús Rodríguez, José García Rey, Angel R. de Lera, STRUCTURAL EFFECTS AFFECTING THE THERMAL ELECTROCYCLIC RING CLOSURE OF VINYLALLENES TO ALKYLIDENECYCLOBUTENES Journal of the American Chemical Society. ,vol. 118, pp. 1881- 1891 ,(1996) , 10.1021/JA9522241
Masahiro Murakami, Hideki Amii, Kenichiro Itami, Yoshihiko Ito, A Remarkable Effect of Silyl Substitution on Electrocyclization of Vinylallenes Angewandte Chemie. ,vol. 34, pp. 1476- 1477 ,(1995) , 10.1002/ANIE.199514761
Hassan Y. Elnagar, William H. Okamura, Thermal [1,7]-sigmatropic hydrogen shift versus electrocyclization of dienylallene sulfoxides Journal of Organic Chemistry. ,vol. 53, pp. 3060- 3066 ,(1988) , 10.1021/JO00248A029