A highly diastereoselective synthesis ofanti-a-allyl-b-fluoroamineshas been developed involving enantioselectivea-fluorination ofaldehydes followed by a diastereoselective Petasis allyl borono-Mannich reaction. The products are obtained generally in goodoverall yields for the two steps and with drs of 97 : 3-99 : 1 and eesof 86-92%. Selected products were converted to 3-, 5- and6-membered ring heterocycles, the latter two types incorporatingan exo-cyclic fluorine.
Chevis, P. J., Wangngae, S., Thaima, T., Carroll, A. W., Willis, A. C., Pattarawarapan, M. & Pyne, S. G. (2019). Highly diastereoselective synthesis of enantioenriched anti-α-allyl-β-fluoroamines. ChemComm, (43), 6050-6053.