Abstract
New atropisomeric 5,6- trans-9,10-dihydrophenanthroline amino- and hydroxy-derivatives 3– 7 possessing two additional stereogenic centres were obtained in high enantiomeric purity by lipase-catalysed kinetic resolution of the corresponding easily accessible racemates. Lipase from Pseudomonas fluorescens (Lipase AK) showed good enantioselectivity ( E > 200) in the esterification reaction of trans-5-azido-6-hydroxyl derivative (±)- 7, giving access to the enantioforms (+)- and (−)- 7 isolated with ee = 97% and ee >98%, respectively. The chemical reduction of azide group furnished the homochiral amino derivatives (+)- and (−)- 4 without a loss in enantiomeric purity. For all the substrates investigated, lipase AK revealed a stereopreference for the enantiomer with a ( P, R, R)-configuration.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
