77857-41-1Relevant academic research and scientific papers
Enantioselective total synthesis of (R)-α- Lipoic acid: An application of thermodynamically controlled deracemization of (±)-2-(2-Methoxyethyl)cyclohexanone
Kaku, Hiroto,Okamoto, Natsuko,Nishii, Takeshi,Horikawa, Mitsuyo,Tsunoda, Tetsuto
, p. 2931 - 2934 (2010)
According to the concept of thermodynamically controlled deracemization, racemic 2-(2-methoxyethyl)cyclohexanone was converted into the R-isomer (99% ee) in 90% yield using (-)-(2R,3R)-trans-2,3-bis(hydroxydiphenylmethyl)-1,4- dioxaspiro[5.4]decane as a host molecule under basic conditions. As an application, a short and enantioselective synthesis of (R) - lipoic acid was accomplished in 44% overall yield from (±)-2-(2-methoxyethyl) cyclohexanone.
A facile and practical method of preparing optically active α-monosubstituted cycloalkanones by thermodynamically controlled deracemization
Kaku, Hiroto,Nakamaru, Aya,Inai, Makoto,Nishii, Takeshi,Horikawa, Mitsuyo,Tsunoda, Tetsuto
experimental part, p. 9450 - 9455 (2011/01/12)
Racemic 2-monosubstituted cycloalkanones were converted to R-isomers when TADDOLs (e.g., 1a, b) were used as host molecules in alkaline aqueous MeOH. The efficiency of this thermodynamically controlled deracemization was strongly influenced by the mixture ratio of the solvent, H2O/MeOH. Based on this finding, an improved method of preparing (R)-2-monosubstituted cycloalkanones with higher optical purity was developed. For example, (R)-2-(4-methylbenzyl)cyclohexanone (5) was obtained in 85% yield with 98% ee, when a 1:1 mixture of H2O/MeOH was used as the solvent in the presence of 1a.
Thermodynamically controlled deracemization of 2-alkylcycloalkanones utilizing host-guest inclusion complexation
Kaku, Hiroto,Ozako, Shinobu,Kawamura, Shiho,Takatsu, Shinobu,Ishii, Masayuki,Tsunoda, Tetsuto
, p. 847 - 850 (2007/10/03)
Based on host-guest inclusion complexation in the solid state, α-substituted cycloalkanones were deracemized using optically active host compound, TADDOL (2a) in alkaline conditions.
Deracemization of 2-alkylcyclohexanones utilizing host-guest molecular association with optically active host compounds in basic suspension media
Tsunoda, Tetsuto,Kaku, Hiroto,Nagaku, Miwa,Okuyama, Etsuko
, p. 7759 - 7760 (2007/10/03)
Based on host-guest inclusion complexation in the solid state, α- substituted cyclohexanones 2α-c were deracemized using optically active host compounds in alkaline conditions to optically active 2 in excellent chemical yield with high enantiomeric excess.
