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

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 wit...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2019-05, Vol.55 (43), p.65-653
Main Authors: Chevis, Philip J, Wangngae, Sirilak, Thaima, Thanaphat, Carroll, Anthony W, Willis, Anthony C, Pattarawarapan, Mookda, Pyne, Stephen G
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Summary: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. A highly diastereoselective synthesis (dr = 99 : 1 97 : 3) of enantioenriched anti -α-allyl-β-fluoroamines (ee = 86-92%) has been developed involving a highly diastereoselective Petasis allyl borono-Mannich reaction of ( S )- or ( R )-α-fluoroaldehydes.
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc02765c