Asymmetric Synthesis and Configurational Stability of C2-Symmetric Hexacoordinated Phosphate Anions (TARPHATs) with Predetermined Chirality from Tartrate Esters

Lacour, Jérôme; Londez, Anne Laurence; Tran, Duy-Hien; Desvergnes-Breuil, Valérie; Constant, Samuel Claude; Bernardinelli, Gérald Hugues

doi:10.1002/1522-2675(200205)85:5%3C1364::AID-HLCA1364%3E3.0.CO;2-Q

Scientific article

English

Asymmetric Synthesis and Configurational Stability of C2-Symmetric Hexacoordinated Phosphate Anions (TARPHATs) with Predetermined Chirality from Tartrate Esters

Contributors

Lacour, Jérôme

; Londez, Anne Laurence; Tran, Duy-Hien; Desvergnes-Breuil, Valérie; Constant, Samuel Claude; Bernardinelli, Gérald Hugues

Published in

Helvetica chimica acta, vol. 85, no. 5, p. 1364-1381

Publication date

2002

Abstract

C2-Symmetric TARPHAT anions 5 made of a central PV atom, one tartrato (=dialkyl 2,3-di(hydroxy-KO)butanedioato(2-)), and two tetrachloropyrocatecholato (=3,4,5,6-tetrachlorobenzene-1,2-diolato(2-)-KO,KO) ligands can be easily prepared in decent to high yields (50-86%) as their dimethylammonium salt by using a one-pot process and simple commercially available starting materials. The presence of the chiral tartrato ligands (usually (2R,3R)) leads to the formation of diastereoisomeric anions ((?,2R,3R)/(?,2R,3R)). Decent to good control by the chiral ligands - under equilibration conditions - over the ? or ? configuration of the adducts was observed (d.r. 84 : 16 in CHCl3 for the di(tert-butyl) tartrate derivative), the selectivity depending on the nature of the ester chains as well as on the solvent.

UNIGE affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

LACOUR, Jérôme et al. Asymmetric Synthesis and Configurational Stability of C2-Symmetric Hexacoordinated Phosphate Anions (TARPHATs) with Predetermined Chirality from Tartrate Esters. In: Helvetica chimica acta, 2002, vol. 85, n° 5, p. 1364–1381. doi: 10.1002/1522-2675(200205)85:5%3C1364::AID-HLCA1364%3E3.0.CO;2-Q

Article

Identifiers

PID : unige:7829
DOI : 10.1002/1522-2675(200205)85:5%3C1364::AID-HLCA1364%3E3.0.CO;2-Q

Journal ISSN

0018-019X

639views

0downloads

Creation

21/06/2010 10:27:59

First validation

21/06/2010 10:27:59

Update

14/03/2023 15:46:52

Status update

14/03/2023 15:46:52

Last indexation

29/10/2024 15:25:30

Asymmetric Synthesis and Configurational Stability of C2-Symmetric Hexacoordinated Phosphate Anions (TARPHATs) with Predetermined Chirality from Tartrate Esters

Contributors

Published in

Publication date

Abstract

UNIGE affiliation entities

Citation (ISO format)

Main files (1)

Identifiers

Journal ISSN

Technical informations

Creation

First validation

Update

Status update

Last indexation