Stereoselective synthesis of chiral hydrocarbazoles via the catalytic Diels–Alder reaction of siloxyvinylindole and cyclic Z-olefin
K Yoshida, T Morikawa, N Yokozuka, S Harada… - Tetrahedron …, 2014 - Elsevier
Abstract The catalytic Diels–Alder reaction of siloxyvinylindole and cyclic Z-olefin derived
from pyroglutamic acid gave optically active substituted hydrocarbazoles. The exo/endo
selectivity of this reaction could be controlled by using an appropriate Lewis acid. Scandium
triflate gave high exo-selectivity and copper triflate gave moderate endo-selectivity.
Subsequent stereoselective alkylation of the cycloadduct led to the synthesis of highly
substituted hydrocarbazoles with five continuous chiral centers including a quaternary …
from pyroglutamic acid gave optically active substituted hydrocarbazoles. The exo/endo
selectivity of this reaction could be controlled by using an appropriate Lewis acid. Scandium
triflate gave high exo-selectivity and copper triflate gave moderate endo-selectivity.
Subsequent stereoselective alkylation of the cycloadduct led to the synthesis of highly
substituted hydrocarbazoles with five continuous chiral centers including a quaternary …
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