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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 2020-08-31T16:57:54Z
dc.date.available 2020-08-31T16:57:54Z
dc.date.issued 2018
dc.identifier.isbn DOI: 10.3390/molecules23040771
dc.identifier.issn 1420-3049
dc.identifier.uri http://dspace.enu.kz/handle/data/15961
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_RU
dc.description.sponsorship GINOP-2.3.2-15-2016-00012 ru_RU
dc.language.iso en ru_RU
dc.publisher Molecules ru_RU
dc.relation.ispartofseries Volume 23, Issue 4;Номер статьи Y
dc.subject sabinol ru_RU
dc.subject terpenoid ru_RU
dc.subject catalyst ru_RU
dc.subject chiral ligand ru_RU
dc.subject triol ru_RU
dc.subject aminodiol ru_RU
dc.subject asymmetric catalysis ru_RU
dc.title Stereoselective Syntheses and Application of Chiral Bi- and Tridentate Ligands Derived from (+)-Sabinol ru_RU
dc.type Article ru_RU

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