Enantiopure N‐Benzyloxycarbonyl‐β 2 ‐amino Acid Allyl Esters from Racemic β‐Lactams by Dynamic Kinetic Resolution using Candida antarctica Lipase B

• Published in: Advanced Synthesis & Catalysis
• Main Authors: Gianolio, Eleonora, Mohan, Resmi, Berkessel, Albrecht
• Other Authors: EC, Marie Curie Research Training Network REVCAT, UoC Excellence Initiative (EG Forum and Interim Jobs), Fonds der Chemischen Industrie
• Format: Article in Journal/Newspaper
• Language: English
• Published: Wiley 2015
• Subjects: Antarc*; Antarctica
• Online Access: http://dx.doi.org/10.1002/adsc.201500820; https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fadsc.201500820; https://onlinelibrary.wiley.com/doi/pdf/10.1002/adsc.201500820

Abstract The dynamic kinetic resolution of α‐substituted racemic β‐lactams by alcoholytic ring‐opening, catalyzed by immobilized lipase B from Candida antarctica is described. With this process, a variety of racemic α‐substituted N ‐Cbz‐azetidinones (Cbz=benzyloxycarbonyl) was transformed to the corresponding N ‐Cbz‐protected β 2 ‐amino acid allyl esters with high enantioselectivity (up to 99%) and high yields (up to quantitative) at room temperature. magnified image