SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 8, 2008, Pages 1260-1264

Samarium diiodide induced reductive coupling of D-threose- and D-erythrose-derived nitrones with methyl acrylate

(5) Rehák, Juraj a Fišera, Lubor a Podolan, Gabriel a Kožíšek, Jozef a Perašínová, Lucia a

a SLOVAK UNIVERSITY OF TECHNOLOGY (Slovakia)

Author keywords

Amino acids; C glycosyl nitrones; Pyrrolidinones; Samarium; Stereoselective synthesis

Indexed keywords

2 PYRROLIDONE DERIVATIVE; ACRYLIC ACID METHYL ESTER; CARBOHYDRATE; ESTER DERIVATIVE; NITRONE DERIVATIVE; PYRROLIDINE DERIVATIVE; SAMARIUM DIIODIDE;

ARTICLE; CHEMICAL REACTION;

EID: 44449109075 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1072732 Document Type: Article

Times cited : (15)

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- Typical Experimental Procedure for Samarium Diiodide Mediated Coupling A stirred and carefully deoxygenated solution of the corresponding nitrone (0.5 mmol) in dry THF (5 mL) was cooled to -78°C under argon. Methyl acrylate and H2O were degassed by boiling under a stream of argon for 20 min. Methyl acrylate (0.7 mmol, H2O (4 mmol, and a solution of SmI2 (15 mL of 0.1 M in THF, 1.5 mmol) were then added. The temperature was kept at -78°C until the reaction was judged to be complete by TLC (2 h, whereupon a sat. aq solution of Na2S2O 3 (40 mL) was added. The mixture was extracted with EtOAc (4 x 30 mL) and the combined organic layers were washed with brine, dried over MgSO 4, filtered, and concentrated in a rotatory evaporator. The residue was purified by silica gel column chromatography using EtOAc-hexanes 1:2
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- Crystal Data C22H35NO4Si, M, 405.60, orthorhombic, P21212 1, a, 7.800(2) Å, 13.749(3) Å, 22.468(5) Å, V, 2409.5(9) Å3, Z, 4, Dx, 1.118 Mg m-3, μ (Mo-Kα, 0.1220 mm-1, F(000, 880, colorless block, 0.305 x 0.492 x 0.739 mm-3, 42540 diffractions measured (Rint, 0.021, 4901 unique, wR2, 0.0951, conventional R, 0.044 on I values of 4507 diffractions with I > 2.0 σ(I, Δ/σ)max, 0.001, S, 1.160 for all data and 254 parameters. Unit cell determination and intensity data collection (θmax, 26.40°) were performed on a Gemini R diffractometer12 at 100 (1) K. Structure solution was direct methods13 and refinements were achieved by full-matrix least-squares m
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