A flexible approach to (R)-3-alkyl-isoindolin-1-ones and (R)-3-aryl-isoindolin-l-ones via a diastereoselective reductive-alkylation is described. Present method is versatile in scope, allowing the easy introduction of...A flexible approach to (R)-3-alkyl-isoindolin-1-ones and (R)-3-aryl-isoindolin-l-ones via a diastereoselective reductive-alkylation is described. Present method is versatile in scope, allowing the easy introduction of various C-3 substituents by Grignard addition to phthalimide derived from (R)-phenylglycinol. 3-Alkyl-3-hydroxy-isoindolin-1-ones can also be obtained in the first step of the present method.展开更多
The enantioseparation of 3-alkyl-isoindolin-1-ones（1—9） and 3-alkyl-3-hydroxy-isoindolin-1-ones（10—14）（R=Me,Et,n-Pr,n-Bu,n-C5H 11 ,n-C7H 15 ,i-Bu,Ph and Bn）,as well as 3-n-heptyl-2-[2-hydroxy-1-phenylethyl]-is...The enantioseparation of 3-alkyl-isoindolin-1-ones（1—9） and 3-alkyl-3-hydroxy-isoindolin-1-ones（10—14）（R=Me,Et,n-Pr,n-Bu,n-C5H 11 ,n-C7H 15 ,i-Bu,Ph and Bn）,as well as 3-n-heptyl-2-[2-hydroxy-1-phenylethyl]-isoindolin-1-one（15） by HPLC using （S）-tert-leucine and （S）-1-α-NEA as a chiral stationary phase,and 1%—6%（volume fraction） 2-propanol or ethanol in hexane as the mobile phase was studied. The effect of content of polar solvent in mobile phase on the enantioseparation was discussed. The effects of 3-substituents on retention factor and chiral recognition were studied. For the majority of racemates（1—14）,a baseline separation could be obtained. For racemate（15）,the elution orders are （3R,1′R）/（3S,1′S） then （3R,1′S）/（3S,1′R） with n-hexane/2-propanol（volume ratio 99∶1） as a mobile phase and the resolutions are 1.44 and 5.58,respectively. [WT5HZ]展开更多
文摘A flexible approach to (R)-3-alkyl-isoindolin-1-ones and (R)-3-aryl-isoindolin-l-ones via a diastereoselective reductive-alkylation is described. Present method is versatile in scope, allowing the easy introduction of various C-3 substituents by Grignard addition to phthalimide derived from (R)-phenylglycinol. 3-Alkyl-3-hydroxy-isoindolin-1-ones can also be obtained in the first step of the present method.
文摘The enantioseparation of 3-alkyl-isoindolin-1-ones（1—9） and 3-alkyl-3-hydroxy-isoindolin-1-ones（10—14）（R=Me,Et,n-Pr,n-Bu,n-C5H 11 ,n-C7H 15 ,i-Bu,Ph and Bn）,as well as 3-n-heptyl-2-[2-hydroxy-1-phenylethyl]-isoindolin-1-one（15） by HPLC using （S）-tert-leucine and （S）-1-α-NEA as a chiral stationary phase,and 1%—6%（volume fraction） 2-propanol or ethanol in hexane as the mobile phase was studied. The effect of content of polar solvent in mobile phase on the enantioseparation was discussed. The effects of 3-substituents on retention factor and chiral recognition were studied. For the majority of racemates（1—14）,a baseline separation could be obtained. For racemate（15）,the elution orders are （3R,1′R）/（3S,1′S） then （3R,1′S）/（3S,1′R） with n-hexane/2-propanol（volume ratio 99∶1） as a mobile phase and the resolutions are 1.44 and 5.58,respectively. [WT5HZ]
