Sythesis of P-chiral compounds
AssigneeTexas Christian University
InventorsJean-Luc Montchamp, Olivier Berger
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Abstract
Shown is the preparation and subsequent elaboration of P-chiral compounds that can be used as a building block for many P-chiral ligands used, for example, in asymmetric catalytic reactions. Specifically, a synthesis is shown for RP(O)(OR*)CH2OH, with R=H, Ph, aryl, alkyl, and R*=menthol (and other chiral alcohol-derived moieties), especially HP(O)(OMen)CH2OH (Men=L-menthol). This versatile building block is easily synthesized via reaction of inexpensive starting materials, H3PO2, menthol as the chiral auxiliary, and paraformaldehyde.
Claims11
A P-chiral building block useful in the preparation of a variety of P-chiral organophosphorus compounds without using halogenated phosphorus starting materials, the building block having the formula:
- wherein the P-chiral building block is made from -(−) menthol as a starting material.
A P-chiral building block useful in the preparation of a variety of P-chiral organophosphorus compounds without using halogenated phosphorus starting materials, the building block having the formula:
- wherein the P-chiral building block is made from -(−) menthol as a starting material.
A P-chiral compound of the formula:
- RP(O)(OR*)CH2OH
- where R═H, Ph, aryl, alkyl, cinnamyl and R*=menthol;
- wherein the compound is made from a starting material having the formula:
- the starting material being crystallized at about −18° C.
A P-chiral compound of the formula:
- RP(O)(OR*)CH2OH
- where R═H, Ph, aryl, alkyl, cinnamyl and R*=menthol;
- wherein the compound is made from a starting material having the formula:
- the starting material being crystallized at room temperature.
A process for the synthesis of asymmetric non-racemic P-chiral compound of the formula:
- RP(O)(OR*)CH2OH
- where R═H, Ph, aryl, alkyl, cinnamyl and R*=menthol;
- wherein the P-chiral compound is made by reacting (−)-menthol, H3PO2 and paraformaldehyde as reactants, followed by crystallization between room temperature and about −18° C. to produce a given yield for the process.
A P-chiral compound of the formula:
- RP(O)(OR*)CH2OH
- where R═H, Ph, aryl, alkyl, cinnamyl and R*=a chiral alcohol selected from the group consisting of menthol, (1R)-endo-(+)-fenchyl alcohol, (−)-borneol and D-(−)-pantolactone.
Dependencies are inferred from the claim text.