Highly diastereoselective synthesis of enantioenriched: Anti -α-allyl-β-fluoroamines

• Main Authors: Philip J. Chevis, Sirilak Wangngae, Thanaphat Thaima, Anthony W. Carroll, Anthony C. Willis, Mookda Pattarawarapan, Stephen G. Pyne
• Format: Journal
• Published: 2019
• Subjects: Chemical Engineering; Chemistry; Materials Science
• Online Access: https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85066149303&origin=inward; http://cmuir.cmu.ac.th/jspui/handle/6653943832/65466
• Institution: Chiang Mai University

© 2019 The Royal Society of Chemistry. A highly diastereoselective synthesis of anti-α-allyl-β-fluoroamines has been developed involving enantioselective α-fluorination of aldehydes followed by a diastereoselective Petasis allyl borono-Mannich reaction. The products are obtained generally in good overall yields for the two steps and with drs of 97:3-99:1 and ees of 86-92%. Selected products were converted to 3-, 5- and 6-membered ring heterocycles, the latter two types incorporating an exo-cyclic fluorine.