A mild access to chiral syn 1,2-diaryl glycols by stereoselective ring opening of ortho substituted trans 2,3-diaryl-oxiranes using Amberlyst 15 in H2O/THF system

Lupattelli, Paolo; Chiummiento, Lucia; Funicello, Maria; Tramutola, Francesco; Marmo, Antonella; Gliubizzi, Natascia; Tofani, Daniela

doi:10.1016/j.tet.2015.06.039

Cited by 10 publications

(4 citation statements)

References 38 publications

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“…Although the lower electrophilicity of aldehydes 5 the reaction appeared very efficient in terms of chemical yield and stereoselectivity for the preparation of the known epoxides 1a , 1c , 1d (entries 1, 3 and 4) and the new ones 1b , 1e and 1f (entries 2, 5 and 6).…”

Section: Resultsmentioning

confidence: 99%

“…Recently the Amb. 15, THF/H 2 O system allowed us to prepare chiral syn ‐glycols stereospecifically from the parent ortho ‐substituted trans 2,3‐diaryloxiranes . The results obtained on substituted diaryloxiranes also showed a dramatic effect of substituent electronic properties on the regioselectivity of the nucleophilic ring opening reaction .…”

Section: Introductionmentioning

confidence: 99%

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Regio‐ and Diastereoselective Organo‐Zinc‐Promoted Arylation of trans‐2,3‐Diaryloxiranes by Arylboronic Acids: Stereoselective Access to trans‐2,3‐Diphenyl‐2,3‐dihydrobenzofuran

et al. 2019

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ortho‐Oxo substituted trans 2,3‐diaryloxiranes were regio‐ and stereoselectively arylated by arylzinc reagents, obtained from the corresponding boronic acids by B–Zn exchange. The reaction was quite general, irrespective to the aryl nucleophile and proceeded via a ring opening at the α‐carbon with respect to the substituted aryl ring. The stereoselectivity was from high to complete toward the alcohol resulted from retention of configuration at the electrophilic carbon. The method allowed a direct and high yielding access to trans 2,3‐diphenyl‐2,3‐dihydrobenzofuran, which is a key structural motif in resveratrol dimers as viniferins. The use of enantioenriched starting diaryloxiranes resulted in no loss of stereochemical integrity in the final trans 2,3‐dihydrobenzofuran, which was characterized for the first time in enantioenriched form.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Regio‐ and Diastereoselective Organo‐Zinc‐Promoted Arylation of trans‐2,3‐Diaryloxiranes by Arylboronic Acids: Stereoselective Access to trans‐2,3‐Diphenyl‐2,3‐dihydrobenzofuran

et al. 2019

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“…Additional references cited within the Supporting Information. [22][23][24][25][26][27][28][29][30][31][32]…”

Section: Supporting Informationmentioning

confidence: 99%

Photocatalytic Cross‐Pinacol Coupling Promoted by Carbon Dioxide**

Okumura

Takahashi

Torii

et al. 2023

Chemistry A European J

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Cross‐pinacol coupling of two different carbonyl compounds was achieved through successive one‐electron transfer processes under photocatalytic conditions. In the reaction, an umpoled anionic carbinol synthon was generated in situ to react nucleophilically with a second electrophilic carbonyl compound. It was revealed that a CO2 additive promoted the photocatalytic generation of the carbinol synthon to suppress undesired radical dimerization. A wide variety of aromatic and aliphatic carbonyl substrates underwent the cross‐pinacol coupling to afford the corresponding unsymmetric vicinal 1,2‐diols, in which even a combination of carbonyl reactants with similar structures such as two aldehydes and two ketones were also well tolerated with high cross‐coupling selectivity.

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“…These spectroscopic data are in accordance with the literature values . [45] trans-2-(3-Nitrophenyl)-3-phenyloxirane (9 g). The Standard Procedure 2 was followed by use of 2-silylphenyl triflate 1 a (105 mg, 0.351 mmol, 1.0 equiv), thioether 7 a (77.6 mg, 0.387 mmol, 1.1 equiv), 3-nitrobenzaldehyde (8 g, 63.6 mg, 0.421 mmol, 1.2 equiv), and CsF (63.9 mg, 0.421 mmol, 1.2 equiv) in acetonitrile (2.5 mL).…”

Section: Trans-2-(2-nitrophenyl)-3-phenyloxirane (9 F)mentioning

confidence: 99%

Domino Processes of Arynes Reacting with Three Classes of Nucleophiles for Organic Syntheses

et al. 2021

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Synthetic application of arynes is broadened by their reactions with neutral N-, Sand nd O-containing nucleophiles to produce three types of compounds. Accordingly, 1,2-dihydroquinolines are synthesized from Schiff bases, alkynes, and arynes through a Diels-Alder reaction. Epoxides are prepared from thioethers and arynes along with aldehydes or ketones through a Johnson-Corey-Chaykovsky reaction. Phenolic ethers are produced from allyl ethers and arynes through a Claisen-type rearrangement. These target molecules, including natural products γ-asarone, asaricin, and a cholesteryl phenolic ether, are formed through reactions initiated by arynes. These new reactions share a prevailing feature of domino processes, which are carried out in a single flask and afford the desired products in good to high yields.

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A mild access to chiral syn 1,2-diaryl glycols by stereoselective ring opening of ortho substituted trans 2,3-diaryl-oxiranes using Amberlyst 15 in H2O/THF system

Cited by 10 publications

References 38 publications

Regio‐ and Diastereoselective Organo‐Zinc‐Promoted Arylation of trans‐2,3‐Diaryloxiranes by Arylboronic Acids: Stereoselective Access to trans‐2,3‐Diphenyl‐2,3‐dihydrobenzofuran

Regio‐ and Diastereoselective Organo‐Zinc‐Promoted Arylation of trans‐2,3‐Diaryloxiranes by Arylboronic Acids: Stereoselective Access to trans‐2,3‐Diphenyl‐2,3‐dihydrobenzofuran

Photocatalytic Cross‐Pinacol Coupling Promoted by Carbon Dioxide**

Domino Processes of Arynes Reacting with Three Classes of Nucleophiles for Organic Syntheses

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