Preparation of chiral indanones and dihydrocoumarins; application to synthesis of (+)-3-(2,6-dimethoxyphenyl) pentanoic acid

Stéphan, Elie; Rocher, Richard; Aubouet, J.; Pourcelot, G.; Cresson, P.

doi:10.1016/s0957-4166(00)80481-4

Cited by 24 publications

(13 citation statements)

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“…Then, 5.00 eq. ethanol (0.234 ml, 4.00 mmol) were added and the reaction mixture was warmed to room temperature and stirred at that temperature for 5 h. Then, the reaction was quenched by adding saturated NH 4 Cl solution (50 mL) and the reaction mixture was diluted with Et 2 O (50 mL). After separation of the organic phase it was dried over MgSO 4 and all volatiles were removed under reduced pressure to give the crude product as a yellow oil.…”

Section: (R)-ethyl 3-(2-hydroxyphenyl)pentanoate (6)mentioning

confidence: 99%

“…When TLC showed full consumption of the starting material, the reaction was quenched by addition of water (100 mL/10 mmol). The mixture was washed with water and brine (50 mL / 10 mmol each), extracted with EtOAc (2x 50 mL / 10 mmol) and the organic phases was dried over MgSO 4 . The crude product was used without further purification.…”

Section: General Procedures For the Methylation Of Salicylic Aldehydesmentioning

confidence: 99%

“…Then, the reaction was quenched by addition of 2.0 mL HCl in Et 2 O (2N). Then, 20 mL saturated aqueous NH 4 Cl solution was added at low temperature and the reaction mixture was allowed to warm to room temperature. Then, it was diluted with Et 2 O (30 mL).…”

Section: -Bromo-2h-chromen-2-one (3d)mentioning

confidence: 99%

“…Then, it was diluted with Et 2 O (30 mL). After washing two times with aqueous saturated NH 4 Cl solution (2x 50 mL) and reextraction of the aqueous layer with Et 2 O (20 mL), the combined organic layers were dried over MgSO 4 . All volatiles were removed under reduced pressure to give the crude product, which was purified by column chromatography (SiO 2 , EtOAc/Pentane) to yield the desired compounds.…”

Section: -Bromo-2h-chromen-2-one (3d)mentioning

confidence: 99%

“…After cooling to room temperature, water (50 mL / 5 mmol) was added and the aqueous layer was extracted twice with CHCl 3 (30 mL / 5 mmol). After drying over MgSO 4 and removal of all volatiles under reduced pressure, the crude mixture was purified by column chromatography (SiO 2 , pentane/EtOAc 8:2) to yield the desired coumarins 3c or 3d.…”

Section: Methyl 3-(5-bromo-2-methoxyphenyl)acrylate (S3b)mentioning

confidence: 99%

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Catalytic asymmetric conjugate addition of Grignard reagents to coumarins—synthesis of versatile chiral building blocks

Teichert

Feringa

2011

Chem. Commun.

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Catalytic asymmetric conjugate addition of Grignard reagents to coumarins-synthesis of versatile chiral building blocks Teichert, J.F.; Feringa, B.L. Take-down policy If you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim.Downloaded from the University of Groningen/UMCG research database (Pure): http://www.rug.nl/research/portal. For technical reasons the number of authors shown on this cover page is limited to 10 maximum. . Data are reported as follows: chemical shifts, multiplicity (s = singlet, d = doublet, t = triplet, q = quartet, br = broad, m = multiplet), coupling constants (Hz), and integration. Optical rotations were measured on a Schmidt + Haensch polarimeter (Polartronic MH8) with a 10 cm cell (c given in g/100 mL). Enantiomeric excesses (ee values) were determined by HPLC analysis using a Shimadzu LC-10ADVP HPLC equipped with a Shimadzu SPD-M10AVP diode array detector and chiral columns as indicated. Ees were determined by comparison of the racemic mixture with the corresponding chiral compounds or the mixtures of both R and S enantiomers. All reactions were carried out under a nitrogen atmosphere using oven dried glassware and using standard Schlenk techniques. CH 2 Cl 2 was dried and distilled over calcium hydride, THF and Et 2 O were dried and distilled over Na/benzophenone. Toluene was dried and distilled over Na. MTBE was dried and distilled over CaH 2 . CuBr•SMe 2 was purchased from Sigma-Aldrich, and used without further purification. Grignard reagents were purchased from Sigma-Aldrich (MeMgBr, EtMgBr, nHexMgBr, i-BuMgBr), all other Grignard reagents were prepared from the corresponding bromides with Mg in Et 2 O. All Grignard reagents were titrated using s-BuOH and catalytic amounts of 1,10-phenanthroline before use. L1 was prepared according to literature, 1 L2-L5 were purchased from Sigma-Aldrich. All coumarins were commercially available, 3c and 3d were prepared (see below). 2.) Synthesis of starting materialsSupplementary Material (ESI)

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Section: (R)-ethyl 3-(2-hydroxyphenyl)pentanoate (6)mentioning

confidence: 99%

Section: General Procedures For the Methylation Of Salicylic Aldehydesmentioning

confidence: 99%

Section: -Bromo-2h-chromen-2-one (3d)mentioning

confidence: 99%

Section: -Bromo-2h-chromen-2-one (3d)mentioning

confidence: 99%

Section: Methyl 3-(5-bromo-2-methoxyphenyl)acrylate (S3b)mentioning

confidence: 99%

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Catalytic asymmetric conjugate addition of Grignard reagents to coumarins—synthesis of versatile chiral building blocks

Teichert

Feringa

2011

Chem. Commun.

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Palladium Nanoparticles‐Catalyzed Synthesis of Indanone Derivatives via Intramolecular Reductive Heck Reaction

Parveen

Sekar

2019

Adv Synth Catal

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An efficient protocol for the straightforward, single-step synthesis of 3-aryl-1-indanones from 2'iodochalcone via reductive Heck reaction using phosphine free, stable and reusable binaphthyl stabilized palladium nanoparticle (Pd-BNP) as a catalyst has been described. An immense array of substrate scope with electron-rich and deficient 2'-iodochalcones have been synthesized. Further derivatization of product indanones have been achieved successfully. The heterogeneous nature of the Pd-BNP has been validated by centrifugation test and mercury poisoning experiment. Pd-BNP has been successfully recycled up to 5 cycles without any significant loss in reaction yield and particle size of nanoparticles, confirmed by TEM analysis. 3-(4-(Trifluoromethyl)phenyl)-2,3-dihydro-1H-inden-1-one(2 r): 78% yield (53.8 mg); Yellow liquid; R f 0.53 (10% ethyl acetate in hexanes); 1 H NMR (400 MHz, CDCl 3 ): δ 2.66 (dd, cm À 1 ; HRMS (m/z): [M + Na] + calcd for C 16 H 11 OF 3 Na: 299.0660; found: 299.0651. 3-(3-Nitrophenyl)-2,3-dihydro-1H-inden-1-one (2 s): 70% yield (44.3 mg); Greenish solid; mp 125°C; R f 0.42 (20% ethyl acetate in hexanes); 1 H NMR (400 MHz, CDCl 3 ): δ 2.66 (dd,

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ChemInform Abstract: Preparation of Chiral Indanones and Dihydrocoumarins; Application to the Synthesis of (+)‐3‐(2,6‐Dimethoxyphenyl)pentanoic Acid (IX).

et al. 1994

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Preparation of chiral indanones and dihydrocoumarins; application to synthesis of (+)-3-(2,6-dimethoxyphenyl) pentanoic acid

Cited by 24 publications

References 5 publications

Catalytic asymmetric conjugate addition of Grignard reagents to coumarins—synthesis of versatile chiral building blocks

Catalytic asymmetric conjugate addition of Grignard reagents to coumarins—synthesis of versatile chiral building blocks

Palladium Nanoparticles‐Catalyzed Synthesis of Indanone Derivatives via Intramolecular Reductive Heck Reaction

ChemInform Abstract: Preparation of Chiral Indanones and Dihydrocoumarins; Application to the Synthesis of (+)‐3‐(2,6‐Dimethoxyphenyl)pentanoic Acid (IX).

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