Lipase‐Catalyzed Doubly Enantioselective Ring‐Opening Resolution between Alcohols and Lactones: Synthesis of Chiral Hydroxyl Esters with Two Stereogenic Centers

• Published in: ChemCatChem
• Main Authors: Xia, Bo, Li, Yanyan, Cheng, Guilin, Lin, Xianfu, Wu, Qi
• Other Authors: National Natural Science Foundation of China, Zhejiang Provincial Natural Science Foundation, Ph.D. Programs Foundation of Ministry of Education of China
• Format: Article in Journal/Newspaper
• Language: English
• Published: Wiley 2014
• Subjects: Antarc*; Antarctica
• Online Access: http://dx.doi.org/10.1002/cctc.201402672; https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fcctc.201402672; https://onlinelibrary.wiley.com/doi/full/10.1002/cctc.201402672

Abstract A novel lipase B from Candida antarctica ‐catalyzed doubly enantioselective ring‐opening resolution between racemic alcohols and lactones was developed. By using this strategy, three optically pure compounds including hydroxyl esters with two stereogenic centers and recovered alcohols and lactones were obtained simultaneously in high yields and ee . This process was used for the resolution of various racemic alcohols with different substituent groups and lactones with different ring sizes (four‐ and seven‐ membered lactones). The scale‐up experiments were also successful. Moreover, molecular docking was performed to explain the molecular basis of this doubly enantioselective ring‐opening resolution. As an attractive and efficient strategy, lipase‐catalyzed doubly enantioselective ring‐opening resolution will be widely used in the synthesis of optically pure hydroxyl esters with two stereogenic centers.