56540-06-8Relevant academic research and scientific papers
Construction of Multiple-Substituted Chiral Cyclohexanes through Hydrogenative Desymmetrization of 2,2,5-Trisubstituted 1,3-Cyclohexanediones
Yu, Chang-Bin,Song, Bo,Chen, Mu-Wang,Shen, Hong-Qiang,Zhou, Yong-Gui
supporting information, p. 9401 - 9404 (2019/11/28)
The construction of chiral multiple-substituted cyclohexanes motifs is a challenging topic in organic synthesis. By the combination of desymmetrization and remote stereocontrol, a ruthenium-catalyzed transfer hydrogenative desymmetrization of 2,2,5-trisubstituted 1,3-cyclohexanediones has been successfully developed for the construction of chiral multiple-substituted cyclohexanes with high enantioselectivity and diastereoselectivity. When an ester group was introduced to the two-position, a hydrogenative desymmetrization/transesterification cascade occurred, affording the bicyclic lactones bearing three stereocenters, including two discrete stereocenters and one quaternary stereogenic center, with high enantioselectivity. The products are the multiple-substituted chiral cyclohexanes bearing the hydroxyl and carbonyl functional groups, which provide a new opportunity for further precise elaboration.
Keto-esters
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, (2008/06/13)
Cyclohexenone esters of the general formula I STR1 or pharmaceutically acceptable acid addition salts thereof, wherein, X is oxygen or sulphur, R1 is 1. alkyl, 2. cycloalkyl, 3. alkenyl, 4. alkynyl, 5. aralkyl, 6. aryl, 7. pyridyl, 8. STR2 or 9. - (CH2)m Y in which Y is perhalogenoalkyl, hydroxy, hydroxyalkoxy, hydroxyalkoxyalkoxy, alkoxy, alkoxyalkoxy, acyloxy or alkoxycarbonyl, or Y is -S(CH2)n OZ, in which Z is acyl, m and n each represent integers of 1 to 3 R2 is 1. hydrogen, 2. alkyl, optionally substituted by alkoxy or alkoxycarbonyl, 3. alkoxycarbonyl, 4. cycloalkyl, 5. cycloalkenyl, 6. aryl, aralkyl, or aralkenyl in which the aryl portion may be substituted by alkyl, alkoxy, alkoxyalkyl, methylenedioxy, alkoxycarbonyl, perhalogenoalkyl, nitro, halogen, nitrile, aryl, dialkylaminocarbonyl, amino, alkylamino, dialkyamino or aralkoxy, 7. a saturated or unsaturated heterocyclic ring containing one or more heteroatoms and which ring may be substituted by alkyl, 8. STR3 OR 9. STR4 R3 is 1. HYDROGEN, 2. alkyl, which may be substituted with alkoxycarbonyl, carboxyl, amino, alkylamino, dialkylamino, or heterocyclic, 3. alkenyl which may be substituted with alkylcarbonyl or alkoxycarbonyl, 4. alkynyl, or 5. aralkyl, R4 is 1. alkyl, 2. alkoxyalkyl, 3. alkenyl, or 4. aralkyl, R5 is Hydrogen, alkyl, aryl or alkoxycarbonyl, and R6 is Hydrogen, alkyl or aryl; With the proviso that when R1 and R4 are ethyl, and R3, R5 and R6 are hydrogen then R2 may not be a methyl. These compounds have biological activity, particularly as anaesthetics.
