CAL-B catalyzed desymmetrization of 3-alkylglutarate: “olefin effect” and asymmetric synthesis of pregabalin
2013
CAL-B catalyzed desymmetrization of prochiral 3-alkylglutaric acid diesters was performed to prepare optically active 3-alkylglutaric acid monoesters bearing various alkyl substituents, including methyl, ethyl, propyl and allyl groups. Allyl esters showed far better stereoselectivity among the alkyl esters, suggesting possible π–π interactions between the olefin of the substrate and the Trp104 or His224 side chains at the enzyme active site. Based on this reaction, the synthesis of (S)-(+)-3-aminomethyl-5-methylhexanoic acid (pregabalin) was achieved with a 70% overall yield.
Keywords:
- Correction
- Source
- Cite
- Save
- Machine Reading By IdeaReader
38
References
17
Citations
NaN
KQI