Enantioselective Photochemical Reactions of N-Phenyl Enaminones in Inclusion Complex Crystals Using a Chiral Host Compound.
Enantioselective reaction of N-methyl-N-phenyl-3-amino-2-cyclohexen-1-one derivatives to the corresponding N-methylhexahydro-4-carbazolones has been accomplished by photolysis in a water suspension of 1:1 inclusion compounds of the starting material with optically active host compounds derived from tartaric acid. 3-(N-Methylanilino)-2,5,5-trimethyl-2-cyclohexen-1-one formed two kinds of dimorphous crystals, and one of these gave an optically active carbazolone derivative by photolysis, but the other one was photochemically inert. X-ray structure analysis showed that two reaction centers, the phenyl and cyclohexenone groups of the reactant, are located in close and distant positions respectively in these two inclusion compounds.
Toda
Fumio
F
Department of Applied Chemistry, Faculty of Engineering, Ehime University, Matsuyama, Ehime 790-8577, Japan, and Department of Chemistry, Faculty of Science, Tokyo Institute of Technology, Ookayama, Meguro-ku, Tokyo 152-8511, Japan.
Miyamoto
Hisakazu
H
Tamashima
Tomoyuki
T
Kondo
Masato
M
Ohashi
Yuji
Y