Cross-linked chiral compounds and methods of making thereof
AssigneeEka Chemicals AB
InventorsRaphaël Duval, Hubert Leveque
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Abstract
The invention relates to a method which comprises synthesizing bifunctional compounds then chiral compounds from the bifunctional compounds, also to synthesizing supports comprising these chiral compounds, and the use of these supports for preparing or separating enantiomers, or for asymmetric synthesis. The invention also relates to bifunctional compounds, their use as a source of functionalized polymers, and to the chiral compounds, also to the use of these chiral compounds in a chiral support in the form of a three-dimensional network or for separating or preparing enantiomers, principally for analytical or preparative chromatography, and in a support for the production of chiral molecules by asymmetric synthesis.
Claims20
A cross-liked chiral compound made by reacting at least one functional group of at least one chiral unit with a compound of the formula 1:
- [RCH═CH—(X)—O]n—Ar—ZY, to create a polymerizable precursor:
- and polymerizing the precursor to create a cross-linked chiral compound where:
- chiral unit is a monomeric, oligomeric, cyclooligomeric or polymeric chiral unit and wherein the unit optionally comprises a primary or secondary amine function or a primary, secondary or tertiary hydroxyl function or a sulphhydryl function and in which all or a portion of these functions have optionally been modified to the ester, amide, urea, carbamate, thioester or thiocarbamate wherein the chiral unit optionally has 2 or more functional groups reactable with a compound of formula I or a compound linkable to a support;
- Ar is an arylene or polyarylene optionally substituted with at least one group selected from the group consisting of alkyl, alkoxy, hydroxyl, trihalogenoalkyl, silyl, thiol, amino, aminoalkyl, amide, nitro, nitrosamino, N-amino, aldehyde, acid and ester groups;
- X is a linear alkylene group carrying more than one carbon atom, a branched alkylene group, or an arylene group, optionally substituted with at least one group selected from the group consisting of alkyl, alkoxy, hydroxyl and trihalogenoalkyl groups;
- R is hydrogen, a linear or branched alkyl group, a linear or branched alkoxy group, a hydroxyl or an aryl group, optionally substituted;
- n is in the range 1 to 20;
- Y is a sulphur or oxygen atom or an amino group;
- and
- Z is a —CH2-group, a —CO-group, —NHCO-group or a —NH—CS-group.
A cross-linked chiral compound having the following formula:
- where
- a chiral unit is a monomeric, oligomeric, cyclooligomeric or polymeric chiral unit and wherein the unit optionally comprises a primary or secondary amine function or a primary, secondary or tertiary hydroxyl function or a sulphhydryl function and in which all or a portion of these functions have optionally been modified to the ester, amide, urea, carbamate, thioester or thiocarbamate wherein the chiral unit optionally has 2 or more functional groups reactable with a compound of formula I or a compound linkable to a support;
- Ar is an arylene or polyarylene optionally substituted with at least one group selected from the group consisting of alkyl, alkoxy, hydroxyl, trihalogenoalkyl, silyl, thiol, amino, aminoalkyl, amide, nitro, nitrosamino, N-amino, aldehyde, acid and ester groups;
- X is a linear alkylene group carrying more than one carbon atom, a branched alkylene group, or an arylene group, optionally substituted with at least one group selected from the group consisting of alkyl, alkoxy, hydroxyl and trihalogenoalkyl groups;
- R is hydrogen, a linear or branched alkyl group, a linear or branched alkoxy group, a hydroxyl or an aryl group, optionally substituted;
- Z is a —CH2— group, a —CO— group, a —NH—CO— group, —NH—CS— group;
- m is 1–20;
- n is 1–20;
- Y is a sulphur or oxygen atom or an amino group;
- L is a silicylene;
- R2 and R3 are independently alkoxy, hydroxyl, trihalogenoalkyl, linear or branched alkyl or aryl groups;
- K is a single bond, a siloxane, or a silane;
- and
- “support” is an organic or mineral support;
- functionalized by an alkene or a hydrogenosilane or a sulphhydryl.
Dependencies are inferred from the claim text.