2005
DOI: 10.1039/b502437d
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Synthetic strategies to chiral organosulfur donors related to bis(ethylenedithio)tetrathiafulvalene

Abstract: Syntheses of enantiopure organosulfur donors by three different strategies requiring only four-six steps are reported. The key step involves either double substitution of an enantiopure cyclic sulfate ester by a dithiolate, attachment of a chiral diol as a ketal, or completely diastereoselective cycloaddition of 1,3-dithiole-2,4,5-trithione to an enantiopure alkene.

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Cited by 37 publications
(28 citation statements)
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“…9 The X-ray crystal structure of 25 indicated strain at the quarternary carbon atom at the fusion with the dithiin ring, and it is probably this factor in the oxo compound which facilitates ring opening with triethyl phosphite. A sensible step would be to make the material without the methyl group at the strained centre, for which apopinene 27 is required as starting material.…”
Section: Synthesis Of Donors 13-16mentioning
confidence: 99%
See 1 more Smart Citation
“…9 The X-ray crystal structure of 25 indicated strain at the quarternary carbon atom at the fusion with the dithiin ring, and it is probably this factor in the oxo compound which facilitates ring opening with triethyl phosphite. A sensible step would be to make the material without the methyl group at the strained centre, for which apopinene 27 is required as starting material.…”
Section: Synthesis Of Donors 13-16mentioning
confidence: 99%
“…3-4, 4 BEDT-TTF derivatives with stereogenic carbon atoms in the molecular skeleton, e.g. 5-8 [5][6][7][8][9][10] , EDT-TTF derivatives containing a chiral oxazoline group such as 9, 11 and an enantioenriched donor 10 containing a stereogenic sulfur atom. 12 A small number of radical cation salts of enantiopure donors have now been characterised and in two cases, (6) 2 PF 6 and (9) 2 AsF 6 , a comparison made between enantiomeric and racemic materials.…”
Section: Introductionmentioning
confidence: 99%
“…Nevertheless, as mentioned earlier, no such evidence has been provided so far in bulk conductors, including the TTF-based materials, although the influence of chirality on the conducting properties of TTF conductors has been indirectly expressed through the modulation of the structural disorder in a few series of conducting radical cation salts based on chiral TTFoxazoline 17,18 or TM-BEDT-TTF donors 19 , in which the enantiopure materials were more conducting than the racemic ones because of the structural disorder present in the latter. Compared with the relatively large number of chiral TTF precursors 16,20 , only a few examples of derived conducting materials have been described, such as those based on TM-BEDT-TTF 13,19,21 dimethyl-bis(ethylenedithio)-TTF (DM-BEDT-TTF) 22,23 , or TTF-oxazoline 17,18 . Moreover, complete series of conducting salts containing both enantiomers and the racemic forms, in order to compare their conducting properties, are even more scarce [17][18][19] , and in all of them the enantiomeric pairs crystallize within the same space group, although there is in principle the possibility that enantiomers crystallize in one of the 11 enantiomorphic space groups, which remains, however, a relatively rare event.…”
mentioning
confidence: 99%
“…We have already reported the total diastereoselectivity of the reactions of the trithione 24 with enantiopure alkenes (-)-α-pinene, (-)-ÎČ-pinene and (+)-2-carene. 11 Encouraged by this, we extended the study to the structurally less complex enantiopure alkene 54 (Scheme 5) which has two stereocentres adjacent to the double bond and four protected hydroxyl groups and which is readily prepared from Dmannitol. 36 Trithione 24 reacted with this alkene to give major (31%) and minor (5%) 1:1 addition products which were assigned structures 55 and 56 respectively, based on the X-ray crystal structure of the minor isomer 56 (Fig.…”
Section: Preparation Of Hydroxyethyl-et 19mentioning
confidence: 99%
“…16 New ET derivatives containing metal binding sites such as 10 with potential for preparing bifunctional materials with magnetic metal ions, [17][18] and an enantiopure donor 11 derived from (-)-ÎČ-pinene have recently been prepared. 11 Cross coupling reactions have been utilised to prepare substituted derivatives of the ethylenedithio-TTF system 12. 19 Furthermore, substituted derivatives of selenium containing donors, such as BETS 20 13, may soon become available following developments in synthetic approaches 21 which will be of interest since some BETS Here we describe the synthesis of a range of ET donors carrying between one and eight hydroxyl groups.…”
mentioning
confidence: 99%