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Organic Letters

Volumn 11, Issue 15, 2009, Pages 3414-3417

Tandem blaise-alkenylation with unactivated alkynes: One-pot synthesis of α-vinylated β-enaminoesters from nitriles

(4) Chun, Yu Sung a Ko, Young Ok a Shin, Hyunik b Lee, Sang Gi a

a Ewha Womans University (South Korea)

b LG Chemical Ltd (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; BROMIDE; NITRILE; ZINC BROMIDE; ZINC DERIVATIVE;

ARTICLE; CHEMISTRY;

ALKYNES; BROMIDES; NITRILES; ZINC COMPOUNDS;

EID: 68149087630 PISSN: 15237060 EISSN: None Source Type: Journal
DOI: 10.1021/ol901241s Document Type: Article

Times cited : (39)

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- When the reaction was workup with 3N aqueous HCl solution, the (α-alkylidene β-ketoester 5 was isolated in 85% yield (see Supporting Information).
- When the reaction was workup with 3N aqueous HCl solution, the (α-alkylidene β-ketoester 5 was isolated in 85% yield (see Supporting Information).

36
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- Similar results were obtained with ethylzinc complex of β-enaminoester, which was prepared in situ from the isolated β-enaminoester and diethylzinc.

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- 3N did not proceeded efficiently, and less than 10% of 4a was obtained after 24 h.
- 3N did not proceeded efficiently, and less than 10% of 4a was obtained after 24 h.

38
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- A typical procedure for the tandem alkenylation of the Blaise reaction intermediate: To a stirred suspension of commercial zinc dust (1.0 g, 15.3 mmol) was added methansulfonic acid (3.7 mg) in anhydrous THF (4.0 mL, After 10 min reflux, benzonitrile (la, 0.8 mL, 7.6 mmol) was added. While maintaining the reflux temperature, ethyl bromoacetate (1.26 mL, 11.4 mmol) was added over 1 h by using a syringe pump, and the reaction mixture was further refluxed for 1 h. To this reaction mixture, phenylacetylene (3a, 0.92 mL, 8.4 mmol) was added, and the reaction mixture was refluxed for 1.5 h. The reaction was quenched with saturated aqueous NH4Cl at room temperature. After evaporation of THF, the residue was extracted with ethyl acetate (20 mL × 3, and the combined organic layer was dried with anhydrous MgSO4 and filtered then concentrated under reduced pressure. The residue was purified by silica chromatography (eluent: ra-hexane/EtOAc, 5:1) to aff
- 2: 294.1494. Found: 294.1500.

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