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Diastereoselective Synthesis of C2-symmetric Hexacoordinated Phosphate Anions (HYPHATs) with Predetermined Chirality from 1,2-Diaryl-ethane-1,2-diols

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Published in Journal of Organometallic Chemistry. 2002, vol. 643-644, p. 392-403
Abstract C2-symmetric HYPHAT anion (5) made of a central phosphorus(V) atom, one hydrobenzoin and two tetracholorocatechol ligands can be simply prepared in high yield as its dimethylammonium salt using a one pot-process and simple commercially available or easily prepared starting materials. The presence of the chiral hydrobenzoin ligands (e.g. R,R) leads to the formation of diastereomeric anions (?,R,R/?,R,R). A partial control over the configuration of the adduct by the chiral ligands is observed (diastereomeric ratio (d.r.) 75:25 in 5% DMSO–CHCl3). This asymmetric induction can be improved (d.r. up to 90:10) by the introduction of ortho bromo substituents on the phenyl rings of the 1,2-diaryl-ethane-1,2-diol ligands.
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Note special issue for F. Mathey
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LACOUR, Jérôme, LONDEZ, Anne Laurence. Diastereoselective Synthesis of C2-symmetric Hexacoordinated Phosphate Anions (HYPHATs) with Predetermined Chirality from 1,2-Diaryl-ethane-1,2-diols. In: Journal of Organometallic Chemistry, 2002, vol. 643-644, p. 392-403. https://archive-ouverte.unige.ch/unige:7759

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Deposited on : 2010-06-21

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