326804-18-6Relevant articles and documents
Ionic-surfactant-coated subtilisin: Activity, enantioselectivity, and application to dynamic kinetic resolution of secondary alcohols
Kim, Kyungwoo,Lee, Eungyeong,Kim, Cheolwoo,Park, Jaiwook,Kim, Mahn-Joo
, p. 8836 - 8844 (2017)
In this work, we explored the utility of ionic-surfactant-coated Bacillus licheniformis subtilisin (ISCBLS) as the catalyst for the dynamic kinetic resolution of secondary alcohols. ISCBLS was prepared by freeze-drying Bacillus licheniformis subtilisin wi
Enantioselective synthesis of α-methyl carboxylic acids from readily available starting materials via chemoenzymatic dynamic kinetic resolution
Thalen, Lisa K.,Sumic, Anna,Bogar, Krisztian,Norinder, Jakob,Persson, Andreas K. Ae.,Baeckvall, Jan-E.
scheme or table, p. 6842 - 6847 (2010/11/24)
An enantioselective method for the synthesis of α-methyl carboxylic acids starting from trans-cinnamaldehyde, a readily available and inexpensive compound, has been developed. Allylic alcohol 1 was obtained via a standard Grignard addition to trans-cinnamaldehyde. Dynamic kinetic resolution was applied to allylic alcohol 1 utilizing a ruthenium catalyst and either an (R)-selective lipase or an (S)-selective protease to provide the corresponding allylic esters in high yield and high ee. A copper-catalyzed allylic substitution was then applied to provide the corresponding alkenes with inversion of stereochemistry. Subsequent C-C double bond cleavage afforded pharmaceutically important α-methyl substituted carboxylic acids in high ee and overall yields of up to 76%.
