Sustainable synthesis of enantiopure fluorolactam derivatives by a selective direct fluorination – amidase strategy. Issue 5 (19th October 2015)

• Record Type: Journal Article
• Authors: Willis, Nicky J.; Fisher, Craig A.; Alder, Catherine M.; Harsanyi, Antal; Shukla, Lena; Adams, Joseph P.; Sandford, Graham
• Is Part Of: Green chemistry. Volume 18:Issue 5(2016)
• Page Start: 1313
• Page End: 1318
• Publication Date: 2015-10-19
• Subjects: Environmental chemistry -- Industrial applications -- Periodicals; Environmental management -- Periodicals; 660
• DOI: 10.1039/c5gc02209f
• Languages: English
• ISSNs: 1463-9262

Abstract

Abstract : Chiral fluorolactam derivatives bearing a fluorine atom at a stereogenic centre were synthesized by a combination of selective direct fluorination using fluorine gas and a biochemical amidase cyclisation process. Abstract : Pharmaceutically important chiral fluorolactam derivatives bearing a fluorine atom at a stereogenic centre were synthesized by a route involving copper catalyzed selective direct fluorination using fluorine gas for the construction of the key C–F bond and a biochemical amidase process for the crucial asymmetric cyclisation stage. A comparison of process green metrics with reported palladium catalyzed enantioselective fluorination methodology shows the fluorination-amidase route to be very efficient and more suitable for scale-up.