Insight into acid-mediated asymmetric spirocyclization in the presence of a chiral diol.
Asymmetric spirocyclization based on intramolecular conjugate addition using a combination of a Lewis acid and an optically active cyclohexane-1,2-diol has been studied in connection with 1) the effect of substituents on the cyclohexane-1,2-diol and 2) the effect of substituents on the substrate. This reaction was found to be both thermodynamically and kinetically controlled under restricted conditions.
Kiguchi
T
T
Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan.
Tsurusaki
Y
Y
Yamada
S
S
Aso
M
M
Tanaka
M
M
Sakai
K
K
Suemune
H
H
D000143:Acids / Q000737:chemistry*; D003511:Cyclohexanols / Q000737:chemistry*; D015394:Molecular Structure; D013057:Spectrum Analysis
D000143:Acids; D003511:Cyclohexanols; C064619:1,2-cyclohexanediol