Novel α-pinene-derived mono- and bisphosphinite ligands: Synthesis and application in catalytic hydrogenation

Hobuß, Dennis; Hasenjäger, Jens; Drießen‐Hölscher, Birgit; Baro, Angelika; Axenov, Kirill V.; Frey, Wolfgang

doi:10.1016/j.ica.2011.01.020

Cited by 12 publications

(13 citation statements)

References 81 publications

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“…In recent years, the discovery and application of new chiral auxiliaries and catalysts have become a crucial question in stereoselective syntheses [ 1 , 2 , 3 , 4 ]. To achieve new, efficient, and commercially available chiral catalysts, natural chiral terpenes [ 5 ], including (+)-pulegone [ 6 , 7 , 8 ], α- and β-pinene [ 9 , 10 , 11 , 12 , 13 , 14 ], and fenchone-camphor [ 15 , 16 , 17 , 18 , 19 ] have proved to be excellent sources. Starting from these readily available natural sources, several powerful chiral catalysts, including various di- and trifunctional synthons, such as 1,3-aminoalcohols and aminodiols, have been applied in stereoselective syntheses [ 5 , 20 ].…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2018

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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.

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Section: Introductionmentioning

confidence: 99%

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

et al. 2018

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“…). The compounds were identified as dehydroabietic acid ( 1 ), 15‐hydroxy‐7‐oxodehydroabietic acid ( 2 ), 7 β ,15‐dihydroxydehydroabietic acid ( 3 ), β ‐ d ‐glucopyranosyl labda‐8(17),13‐diene‐(15,16)‐lactone‐19‐oate ( 4 ), 7 α ,15‐dihydroxydehydroabietic acid ( 5 ), (1 S ,2 S ,4 R )‐(+)‐limonene‐1,2‐diol ( 6 ), sobrerol ( 7 ), and 4‐hydroxy‐benzoic acid ( 8 ) by comparing their spectroscopic data, including 1 H‐ and 13 C‐NMR, with previously reported values and MS data. To the best of our knowledge, this study provides the first example of compounds 3 – 7 being isolated from P. koraiensis .…”

Section: Resultsmentioning

confidence: 99%

Pinecone of Pinus koraiensis Inducing Apoptosis in Human Lung Cancer Cells by Activating Caspase‐3 and its Chemical Constituents

Lee

Roh

et al. 2017

Chemistry & Biodiversity

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Pinecones from Pinus koraiensisSiebold & Zucc. (Pinaceae), which have historically been treated as an undesired waste by-product in the processing of seeds, have recently been shown to contain ingredients with potent biological activities, such as polyphenols exhibiting antitumor activity. With this study, we seek to broaden our understanding of antitumor compounds contained in these pinecones beyond just polyphenols. We found that the water extract of P. koraiensis pinecones exhibits significant cytotoxic activity, with IC values ranging from 0.62 to 1.73 mg/ml in four human lung cancer cell lines, A549, H1264, H1299, and Calu-6, irrespective of their p53 status. We also demonstrate that pinecone water extract induces apoptosis associated with caspase-3 activation in the same cancer cell lines. Chemical investigation of the pinecone water extract revealed eight main components (1 - 8), and their structures were identified as dehydroabietic acid (1), 15-hydroxy-7-oxodehydroabietic acid (2), 7β,15-dihydroxydehydroabietic acid (3), β-d-glucopyranosyl labda-8(17,13)-diene-(15,16)-lactone-19-oate (4), 7α,15-dihydroxydehydroabietic acid (5), (+)-(1S,2S,4R)-limonene-1,2-diol (6), sobrerol (7), and 4-hydroxybenzoic acid (8). These findings suggest a novel biological application of P. koraiensis pinecones in combatting human lung cancer, and further identify the major compounds that could contribute to this anticancer activity.

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“…All of the starting materials (glycols) are known compounds. Several of them were prepared according to the literature ( cis - 1a , trans - 1a , 1b , 1c , and 1d ), and one was purchased as a commercial reagent [benzopinacol ( 1j )]. Glycols 1e , 1f , 1g , 1h , and 1j were prepared via the following procedures.…”

Section: Methodsmentioning

confidence: 99%

Sodium Hypochlorite Pentahydrate as a Reagent for the Cleavage of trans-Cyclic Glycols

et al. 2019

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Sodium hypochlorite pentahydrate (NaOCl•5H 2 O) can be used toward the efficient glycol cleavage of trans-cyclic glycols, which are generally resistant to this transformation. Interestingly, the reaction of cis-cyclic glycols with NaOCl•5H 2 O is slower than that observed for the corresponding transisomer. This trans selectivity is in sharp contrast to traditional oxidants used for glycol cleavage. Acyclic glycols can also react efficiently with NaOCl•5H 2 O to form their corresponding carbonyl compounds in high yield.

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Novel α-pinene-derived mono- and bisphosphinite ligands: Synthesis and application in catalytic hydrogenation

Cited by 12 publications

References 81 publications

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

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

Pinecone of Pinus koraiensis Inducing Apoptosis in Human Lung Cancer Cells by Activating Caspase‐3 and its Chemical Constituents

Sodium Hypochlorite Pentahydrate as a Reagent for the Cleavage of trans-Cyclic Glycols

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