We describe an efficient and convenient route for the preparation of enantiomerically pure D-labelled histidine by asymmetric hydrogenation with a Rh-diphosphine complex in the presence of strong non-coordinating acids. A single-crystal neutron diffraction study of the selectively dideuterated N-benzoyl-histidine methyl ester, tetrafluoroborate salt determined the absolute stereochemistry. This allowed us to clarify the role of H+ in the whole reduction process.
Histidine and deuterium-labelled histidine by asymmetric catalytic reduction and assignment of the absolute stereochemistry by neutron diffraction / A. Albinati, E. Cesarotti, S.A. Mason, I. Rimoldi, S. Rizzato, D.S. Zerla. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 21:9-10 (Sp. Iss. SI)(2010 May), pp. 1162-1165. [10.1016/j.tetasy.2010.03.044]
Histidine and deuterium-labelled histidine by asymmetric catalytic reduction and assignment of the absolute stereochemistry by neutron diffraction
A. Albinati;E. Cesarotti;I. Rimoldi;S. Rizzato;D.S. Zerla
2010
Abstract
We describe an efficient and convenient route for the preparation of enantiomerically pure D-labelled histidine by asymmetric hydrogenation with a Rh-diphosphine complex in the presence of strong non-coordinating acids. A single-crystal neutron diffraction study of the selectively dideuterated N-benzoyl-histidine methyl ester, tetrafluoroborate salt determined the absolute stereochemistry. This allowed us to clarify the role of H+ in the whole reduction process.Pubblicazioni consigliate
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