Reversal of facial selectivity in complex Diels-Alder reactions.
A complex Diels-Alder reaction between a semi-cyclic diene with allylic silyloxy substituents and a bromo enone presented an unusual diastereoselectivity: attack of the diene occured on its more hindered face, and this reversal of selectivity was shown to be induced by the presence of a bromo substituent in the dienophile.
Funel
Jacques-Alexis
JA
Laboratoire de Synthèse Organique, UMR CNRS 7652, Ecole Polytechnique, DCSO, Palaiseau, France.
Ricard
Louis
L
Prunet
Joëlle
J
D000466:Alkadienes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D008968:Molecular Conformation; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000466:Alkadienes; D011083:Polycyclic Compounds