Journal
SYNLETT
Volume -, Issue 7, Pages 1139-1142Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-2007-977437
Keywords
asymmetric catalysis; fluorine; alpha-cyanophosphonate; palladium; medicinal chemistry
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We describe herein the catalytic asymmetric fluorination of alpha-cyanophosphonates using chiral Pd(II)-bisphosphine complexes. While metal complexes failed to promote the reaction alone, a reaction system involving Pd(II) and organic base such as 2,6-lutidine was developed. The Pd(II) complex activates the substrates through coordination of the nitrile group, and 2,6-lutidine abstracts an acidic proton, thereby affording the desired fluorinated products in good yields with up to 78% ee. The products may be useful as novel physiological phosphate mimics in medicinal chemistry.
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