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Stereoselective Syntheses and Application of Chiral Bi- and Tridentate Ligands Derived from (+)-Sabinol

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dc.contributor.author Tashenov, Yerbolat
dc.contributor.author Daniels, Mathias
dc.contributor.author Robeyns, Koen
dc.contributor.author Meervelt, Luc Van
dc.contributor.author Dehaen, Wim
dc.contributor.author Suleimen, Yerlan M.
dc.contributor.author Szakonyi, Zsolt
dc.date.accessioned 2024-09-24T11:02:11Z
dc.date.available 2024-09-24T11:02:11Z
dc.date.issued 2018
dc.identifier.issn 1420-3049
dc.identifier.other doi:10.3390/molecules23040771
dc.identifier.uri http://rep.enu.kz/handle/enu/16911
dc.description.abstract A library of bidentate diols, as well as tridentate triols and aminodiols, derived from (+)-sabinol, was synthesized in a stereoselective manner. Sabinol was transformed into allylic trichloroacetamide via Overman rearrangement of the corresponding trichloroacetimidate. After changing the protecting group to Boc, the enamine was subjected to stereospecific dihydroxylation with OsO4/NMO, resulting in the (1R,2R,3R,5R)-aminodiol diastereomer. The obtained primary aminodiol was transformed to a secondary analogue. The ring closure of the N-benzyl-substituted aminodiol with formaldehyde was investigated and regioselective formation of the spiro-oxazolidine ring was observed. Hydroboration or dihydroxylation of sabinol or its benzyl ether with OsO4/NMO resulted in the formation of sabinane-based diols and triols following a highly stereospecific reaction. Treatment of sabinol with m-CPBA afforded O-benzoyl triol as a diastereoisomer of the directly dihydroxylated product, instead of the expected epoxy alcohol. The resulting aminodiols, diol, and triols were applied as chiral catalysts in the reaction of diethylzinc and benzaldehyde from moderate to good selectivity. ru
dc.language.iso en ru
dc.publisher Molecules ru
dc.relation.ispartofseries 23;771
dc.subject sabinol ru
dc.subject terpenoid ru
dc.subject catalyst ru
dc.subject chiral ligand ru
dc.subject triol ru
dc.subject aminodiol ru
dc.subject asymmetric catalysis ru
dc.title Stereoselective Syntheses and Application of Chiral Bi- and Tridentate Ligands Derived from (+)-Sabinol ru
dc.type Article ru


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