Process for the preparation of an enantiomerically and/or diastereomerically enriched ester, thioester, alcohol or thiol
OwnerGerardus Karel Maria Verzijl, Peter Jan Leonard Mario Quaedflieg +1inventors
InventorsGerardus Karel Maria Verzijl, Peter Jan Leonard Mario Quaedflieg, Quirinus Bernardus Broxterman
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Abstract
The invention relates to a process for preparing an enantiomerically and/or diastereomerically enriched ester or thioester having at least two adjacent chiral centres, wherein a mixture of stereoisomers of a secondary alcohol or thiol having a structure comprising a first chiral center forming a secondary alcohol or secondary thiol moiety in the beta position relative to a second chiral center having one hydrogen substituent, is reacted with an acyl donor in the presence of an epimerisation catalyst and a stereoselective acylation catalyst.
Claims22
Process for preparing an enantiomerically and/or diastereomerically enriched ester or thioester having at least one pair of two adjacent chiral centres, wherein a mixture of stereoisomers of a secondary alcohol or thiol having a structure comprising a first chiral center forming a secondary alcohol or secondary thiol moiety in the beta position relative to a second chiral center having one hydrogen substituent and not forming a secondary alcohol moiety, is reacted with an acyl donor in the presence of an epimerisation catalyst and a stereoselective acylation catalyst.
(canceled)
Process for preparing an enantiomerically and/or diastereomerically enriched ester or thioester having at least one pair of two adjacent chiral centers, wherein a mixture of stereoisomers of a secondary alcohol or thiol having a structure comprising a first chiral center forming a secondary alcohol or secondary thiol moiety in the beta position relative to a second chiral center having one hydrogen substituent and nor forming a secondary alcohol moiety, wherein the second chiral center forms an amine moiety, an alkyl moiety or a secondary thiol moiety, wherein the first chiral centre and the second chiral centre are part of a cyclopentyl, cyclohexyl, cycloheptyl, pyrolidyl, piperidinyl or tetrahydrofuryl moiety, is reacted with an acyl donor in the presence of an epimerisation catalyst and a stereoselective acylation catalyst, wherein the epimerisation catalyst is based on a metal selected from the group of ruthenium, iridium, aluminum, samarium and scandium, the metal being in an oxidation state equal to or higher than 1, wherein the stereoselective acylation catalyst is hydrolase.
Process for preparing an enantiomerically and/or diastereomerically enriched ester or thioester having at least one pair of two adjacent chiral centers, wherein a mixture of stereoisomers of a secondary alcohol or thiol having a structure comprising a first chiral center forming a secondary alcohol or secondary thiol moiety in the beta position relative to a second chiral center having one hydrogen substituent and not forming a secondary alcohol moiety, wherein the second chiral center is attached to three carbon atoms, wherein the first chiral centre and the second chiral centre are part of a cyclopentyl, cyclohexyl, cycloheptyl, pyrolidyl, piperidinyl or tetrahydrofuryl moiety, is reacted with an acyl donor in the presence of an epimerisation catalyst and a stereoselective acylation catalyst, wherein the epimerisation catalyst is based on a metal selected from the group of ruthenium, iridium, aluminum, samarium and scandium, the metal being in a oxidation state equal to or higher than 1, wherein the stereoselective acylation catalyst is a hydrolase.
Dependencies are inferred from the claim text.