SCOPUS 정보 검색 플랫폼

Volumn , Issue 4, 2007, Pages 658-660

Intermolecular cycloaddition of ethyl glyoxylate O-tert- butyldimethylsilyloxime with alkenes

(8) Tamura, Osamu a Morita, Nobuyoshi a Takano, Yuu a Fukui, Kenji a Okamoto, Iwao a Huang, Xin b Tsutsumi, Yoshiyuki b Ishibashi, Hiroyuki b

a SHOWA PHARMACEUTICAL UNIVERSITY (Japan)

b KANAZAWA UNIVERSITY (Japan)

Author keywords

Alkenes; Boron trifluoride; Cycloaddition; Cycloadducts; N boranonitrone

Indexed keywords

ALKENE DERIVATIVE; ETHYL GLYOXYLATE O TERT BUTYLDIMETHYLSILYLOXIME; ISOXAZOLIDINE DERIVATIVE; NITRONE DERIVATIVE; OXIME DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; POLYMERIZATION; ROOM TEMPERATURE;

EID: 33947226546 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-967939 Document Type: Article

Times cited : (13)

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26
- 33947249161
- Preparation of Ethyl 2-[tert- Butyldimethylsilyloxyimino]acetate (12, The mixture of ethyl 2-hydroxyiminoacetate (11;11 0.91 g, 7.8 mmol, tert- butylchlorodimethylsilane (1.77 g, 11.8 mmol, and imidazole (1.60 g, 23.5 mmol) in DMF (12 mL) was stirred at r.t. for 46 h. The reaction mixture was poured into H2O and extracted with Et2O. The combined organic phases were washed with brine and dried with MgSO4. The solvent was removed by rotary evaporation and the crude product was purified by column chromatography on silica gel with hexane-Et2O (20:1) to afford 12 (1.77 g, 98, as a colorless oil. IR: 2934, 1749, 1728 cm -1. 1H NMR (300 MHz, CDCl3, δ, 7.62 (s, 1 H, 4.30 (q, J, 7.1 Hz, 2 H, 1.33 (t, J, 7.1 Hz, 3 H, 0.95 (s, 9 H, 0.23 (s, 6 H, 13C NMR 75 MHz, CDCl3, δ, 162.3, 146.1, 61.3, 25.7, 18.0, 14.0, 5
- 3Si: 231.1291; found: 231.1270.

27
- 33947249683
- Typical Procedure for the Cycloaddition: To a solution of 12 (300 mg, 1.3 mmol) in DCE (10 mL) were added 7e (1.1 mL, 13 mmol) and BF3·OEt2 (310 μL, 2.9 mmol) at r.t, and then the mixture was heated at 60°C for 2 h. The reaction was monitored by TLC. After cooling, the reaction mixture was poured into sat. NaHCO 3 solution and was extracted with CHCl3. The combined organic layers were washed with brine and dried with MgSO4. The residue was concentrated under reduced pressure. The crude product was purified by chromatography on silica gel with hexane-EtOAc (3:2) to give two diastereomers, 14e (160 mg, 61, and 14e′ (47 mg, 18, as light brown oils. 14e: IR (neat, 1733 cm-1. 1H NMR (300 MHz, CDCl3, δ, 5.90 (br s, 1 H, 4.23 (q, J, 7.1 Hz, 2 H, 4.12 (d, J, 7.5 Hz, 1 H, 2.73 dd, J, 7.0, 14.5 Hz, 1 H, 1.82
- 3): δ = 171.3, 96.1, 70.2, 61.4, 59.5, 38.5, 32.2, 24.4, 23.5, 14.1.

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- Tamura, O.¹ Shiro, T.² Ogasawara, M.³ Toyao, A.⁴ Ishibashi, H.⁵

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