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

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Abstract

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.

Graphical abstract: Highly diastereoselective synthesis of enantioenriched anti-α-allyl-β-fluoroamines

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Publication details

The article was received on 10 Apr 2019, accepted on 30 Apr 2019 and first published on 30 Apr 2019


Article type: Communication
DOI: 10.1039/C9CC02765C
Chem. Commun., 2019, Advance Article

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

    P. J. Chevis, S. Wangngae, T. Thaima, A. W. Carroll, A. C. Willis, M. Pattarawarapan and S. G. Pyne, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9CC02765C

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