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P,N-Bidentate Phosphorus Derivatives of (S)-Prolinol

Authors:	Polosukhin A I Bondarev O G Lyubimov S E Shiryaev A A Petrovskii P V Lysenko K A Gavrilov K N

Institution:	(1) Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, ul. Vavilova 28, Moscow, 117813, Russia;(2) Esenin State Pedagogical University, Ryazan, Russia

Abstract:	Phosphorylation of (S)-prolinol with P(NEt₂)₃was used to synthesize aminophosphite (2R,5S)- ${\text{HCH}}_{\text{2}} {\text{OPNEt}}_{\text{2}}$ , which was reacted with the corresponding amino alcohols to afford (2S,5R)- ${\text{CH}}_{\text{2}} \left( {{\text{CH}}_{\text{2}} } \right)_2 {\text{NCHCH}}_{\text{2}} {\text{OPO}}\left( {{\text{CH}}_{\text{2}} } \right)_2 {\text{NMe}}_{\text{2}}$ (Va) and (2S,5R)- ${\text{CH}}_{\text{2}} \left( {{\text{CH}}_{\text{2}} } \right)_2 {\text{NCHCH}}_{\text{2}} {\text{OPO}}\left( {{\text{CH}}_{\text{2}} } \right)_2 {\text{N}}\left( {{\text{CH}}_{\text{2}} } \right)_{\text{4}} {\text{CH}}_{\text{2}}$ (Vb). Reaction of Vawith Rh(CO)₂Cl]₂(P/Rh = 1) yields the mononuclear chelate Rh(CO)(P^N)Cl] (VIIa), while the analogous reaction with Vbresults in a mixture of products with cis- and trans-orientation of the coordinated phosphorus and nitrogen atoms. Spectral characteristics of the products of coordination of ligands Vaand Vbwere compared with those for the binuclear reference complex Rh(CO)(L)Cl]₂(VIII), where L is P-monodentate ligand (2S,5R)- ${\text{CH}}_{\text{2}} \left( {{\text{CH}}_{\text{2}} } \right)_2 {\text{NCHCH}}_{\text{2}} {\text{OPOEt}}_{\text{2}}$ (VI). The ligands and complexes were studied by IR, NMR, ³¹P and ¹³C spectroscopy, mass spectrometry, and elemental analysis methods. X-ray diffraction analysis of crystals VIIIwas performed.

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