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UNIVERSITA’ DEGLI STUDI DI MILANO PhD IN CHEMICAL SCIENCES XXII CYCLE

UNIVERSITA’ DEGLI STUDI DI MILANO PhD IN CHEMICAL SCIENCES XXII CYCLE. Natural and unnatural aminoacids by catalytic reduction with Rh(I)-diphosphine complexes; role of strong acids in the synthesis of deuterium labelled histidine. Daniele Sergio ZERLA Matr. R07227.

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UNIVERSITA’ DEGLI STUDI DI MILANO PhD IN CHEMICAL SCIENCES XXII CYCLE

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  1. UNIVERSITA’ DEGLI STUDI DI MILANO PhD IN CHEMICAL SCIENCES XXII CYCLE Natural and unnatural aminoacids by catalytic reduction with Rh(I)-diphosphine complexes; role of strong acids in the synthesis of deuterium labelled histidine. Daniele Sergio ZERLA Matr. R07227 Tutor: Chiar.mo Prof. E.CESAROTTI

  2. [PP(Rh)COD]+ClO4- + Solv. HBF4 D2 I_Synthesis of histidine and deuterium labelled histidine D-Histidine Unnatural labelled carnosine

  3. II_Use of different strong non coordinating acids in the synthesis of histidine by asymmetric catalytic reduction ACIDS HBF4 CF3SO3H HClO4 CH3SO3H hydrogenation deuteration Different ligands Different solvent Different substrate/acid molar ratio

  4. HYDROGENATION

  5. DEUTERATION

  6. FURTHER CRYSTALLIZATIONS

  7. PRECIPITATION DURING REACTION CH3OH or CH3OD H2 or D2 HBF4 or HClO4 0.05 M methanol solution Optically pure product as white solid salt (45-55% yield) Is the catalyst active after reaction?

  8. RECYCLE OF CATALYST H2 or D2 Solution containing catalyst Yes, the catalyst was still active after first reaction Catalyst solution was recycled 5 time without loss of enantioselectivity

  9. work in progress DPEN BINAP AMPY BDPP ZEDPHOS PANDA

  10. PANDA ampy DPEN Asymmetric Transfer Hydrogenation (ATH) of simple ketones catalysed by Ru(II)/diphosphine/diamine complexes DIAMINE

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