Environmentally Friendly, Efficient Resolution of Racemic Secondary Alcohols by Lipase‐Catalyzed Enantioselective Transesterification in Ionic Liquids in the Presence of Organic Bases

• Published in: Chemistry & Biodiversity
• Main Authors: Wu, Xiao‐Mei, Xin, Jia‐Ying, Sun, Wei, Xia, Chun‐Gu
• Format: Article in Journal/Newspaper
• Language: English
• Published: Wiley 2007
• Subjects: Antarc*; Antarctica
• Online Access: http://dx.doi.org/10.1002/cbdv.200790023; https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fcbdv.200790023; https://onlinelibrary.wiley.com/doi/pdf/10.1002/cbdv.200790023

Abstract The lipase‐catalyzed enantioselective transesterification of racemic secondary alcohols was studied using vinyl acetate as acyl donor in two imidazolium‐based ionic liquids vs. hexane ( Scheme ), both in the absence and presence of catalytic amounts of organic bases such as triethylamine (Et 3 N) or pyridine. The organic bases generally enhanced both the rate and enantioselectivity of the reaction. Further, the system 1‐butyl‐3‐methyl‐1 H ‐imidazolium hexafluorophosphate/ Candida antarctica lipase B ([bmim][PF 6 ]/CALB) could be readily recycled four times without significant loss in activity or enantioselectivity ( Table 4 ).