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Tobias Möller – EWPC 2013

Tobias Möller Universität Leipzig Prof. Dr. E. Hey-Hawkins. Tobias Möller – EWPC 2013. Chiral Phosphane Ligands?. ( S , S )-DIOP. Josiphos. ( R , R )-DIPAMP. ( S )-BINAP. Chiral Carbon Backbone. P -Chirality. Tobias Möller – EWPC 2013. Principles. Desymmetrisation.

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Tobias Möller – EWPC 2013

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  1. Tobias Möller Universität Leipzig Prof. Dr. E. Hey-Hawkins Tobias Möller – EWPC 2013

  2. Chiral Phosphane Ligands? (S,S)-DIOP Josiphos (R,R)-DIPAMP (S)-BINAP Chiral Carbon Backbone P-Chirality Tobias Möller – EWPC 2013

  3. Principles Desymmetrisation P-Chiral Phosphanes: Novel Synthetic Approaches Face differentiation Tobias Möller – EWPC 2013

  4. Desymmetrisation • yield: 40-70% • good to high selectivities • diastereomers easily separable Tobias Möller – EWPC 2013

  5. Desymmetrisation repulsive attractive P S repulsive O C 180° R exo endo Tobias Möller – EWPC 2013

  6. Face differentiation Tobias Möller – EWPC 2013

  7. Face differentiation • yield: 87-90% • good to high selectivities • diastereomers easily separable F. Mathey, Acc. Chem. Res., 2004, 37, 954-960; T. Möller, M. B. Sárosi, E. Hey-Hawkins, Chem. Eur. J., 2012, 18, 16604-16607 Tobias Möller – EWPC 2013

  8. Face differentiation C3 C2’ [0.23] 180° C3 [0.26] attractive attractive C3 C2‘ C2‘ C3‘ C3‘ C3’ [0.42] P1 [0.36] P repulsive O C R endo-regio-1 endo-regio-2 T. Möller, M. B. Sárosi, E. Hey-Hawkins, Chem. Eur. J., 2012, 18, 16604-16607 Tobias Möller – EWPC 2013

  9. Face differentiation Determination of stereochemistry: Crystal structure analysis Main Diastereomers 5c 2b P212121 Z = 4 wR2 = 0.0783 Flack parameter: −0.07(3) P212121 Z = 4 wR2 = 0.0878 Flack parameter: −0.02(7) T. Möller, M. B. Sárosi, E. Hey-Hawkins, Chem. Eur. J., 2012, 18, 16604-16607 Tobias Möller – EWPC 2013

  10. Face differentiation Determination of stereochemistry: Selective 1D-NOE-NMR 5c T. Möller, M. B. Sárosi, E. Hey-Hawkins, Chem. Eur. J., 2012, 18, 16604-16607 Tobias Möller – EWPC 2013

  11. Face differentiation C2 Z = 4 wR2 = 0.0682 Flack parameter: −0.04(4) Tobias Möller – EWPC 2013

  12. Face differentiation (✔) ✔ (✔) Catalysis ✔ ✔ Tobias Möller – EWPC 2013

  13. Acknowledgement • SMWK (Landesgraduiertenstipendium) • Chemetall • PhoSciNet • b AK Hey-Hawkins Tobias Möller – EWPC 2013

  14. Tobias Möller – EWPC 2013

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