Stereoselective synthesis of Baylis-Hillman-type adducts via allenolates generated by acyl migration.
[reaction: see text] The rearrangement of the carbamoyl group in allenyl carbamate 1 in the presence of n-BuLi in situ generates the allenolate 3, which is subsequently intercepted with aromatic aldehydes furnishing (Z)- or (E)-configured Baylis-Hillman-type adducts 4 or 5. The double bond isomers can be interconverted by a retro aldol-type reaction.
Gudimalla
Nagaraju
N
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, D-48149 Münster, Germany.
Fröhlich
Roland
R
Hoppe
Dieter
D