Synthesis and Characterisation of Monophosphines and Aminophosphines Bearing Chiral Phosphetane Units

Abstract

Enantiomerically pure monophosphines bearing phosphetane units have been prepared from primary phosphines and the cyclic sulfates of anti-1,3-diols. Various substituents have been introduced on both the phosphorus and the ring carbon atoms, thus showing the high flexibility of the synthetic approach. The same synthetic method has been applied to the preparation of P-N heterobidentate ligands bearing phosphetane and azetidine rings. The final products have been characterised by X-ray diffraction studies.

Key words

phosphorus - heterocycles - metallocenes - transition metals - asymmetric catalysis

References

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5

³¹P NMR (CDCl₃): δ = 56. ¹H NMR (CDCl₃): δ = 2.9-3.4 (m, 2 H), 4.0-4.3 (m, 2 H), 7.1-7.9 (C₆H₅). ¹³C NMR (CDCl₃): δ = 31.7 (d, J = 10.6 Hz, CH₂), 40.5 (d, J = 36.6 Hz, CH).

27

Ferrocenylphosphine: ³¹P NMR (C₆D₆): δ = -145. ¹H NMR (C₆D₆): δ = 3.80 (d, J _H-P = 199 Hz, PH), 3.96 (s, 5 H, Cp), 4.01 (m, 2 H, CH), 4.10 (m, 2 H, CH).