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Volumn 48, Issue 13, 2007, Pages 2345-2348

Stereoselective synthesis of trans-olefins by the copper-mediated SN2′ reaction of vinyl oxazines with Grignard reagents. Asymmetric synthesis of d-threo-sphingosines

Author keywords

Grignard reagents; Oxazine; Regioselective asymmetric aminohydroxylation; SN2 Reaction; Sphingosine

Indexed keywords

ALKENE DERIVATIVE; COPPER; GRIGNARD REAGENT; OXAZINE DERIVATIVE; REAGENT; SPHINGOSINE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

EID: 33847287703     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.01.145     Document Type: Article
Times cited : (17)

References (50)
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    • N2′ reactions:. Kar A., and Argade N.P. Synthesis (2005) 2995-3022
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    • see, for other similar approaches:
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    • Morgan, A.J.1    Masse, C.E.2    Panek, J.S.3
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    • note
    • N2′ reaction of vinyl oxazine with Grignard reagents: A flame dried two-necked flask was charged with cuprous cyanide (8.5 mg, 0.1 mmol) and dry ether (10 mL) under nitrogen atmosphere. The reaction flask was cooled to 0 °C in ice-salt mixture and a solution of Grignard reagent in ether (1 M, 0.5 mL, 0.5 mmol) was added dropwise. After stirring for 10 min, a solution of vinyl oxazine (79 mg, 0.2 mmol) in ether was added dropwise through cannula for 10 min. The reaction mixture was stirred for an additional hour, and then brought to room temperature and stirred for another 1 h. After the complete disappearance of the starting material on TLC, the brownish reaction mixture was quenched with saturated ammonium chloride, extracted with ethyl ether (3 × 20 mL), washed with water, and dried over anhydrous sodium sulfate. The solvents were removed in vacuo and the residue was purified by flash column chromatography on silica gel (ethyl acetate-hexane, 3:1) to afford the respective protected N-acetylsphingosines 7a-e.
  • 34
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    • note
    • 3): δ 169.81, 159.35, 154.12, 152.84, 136.07, 130.37, 129.49, 126.67, 115.70, 114.75, 113.86, 76.79, 70.12, 66.91, 55.75, 55.23, 52.34, 32.32, 31.92, 29.69, 29.50, 29.22, 23.28, 22.67, 14.03.
  • 37
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    • For the biological activities of sphingosines:. Vance D.E., and Vance J.E. (Eds), Elsevier Science B.V., Amsterdam Chapter 12, pp 309-339
    • For the biological activities of sphingosines:. Merrill Jr. A.H., and Sweeley C.C. In: Vance D.E., and Vance J.E. (Eds). Biochemistry of Lipids, Lipoproteins and Membranes (1996), Elsevier Science B.V., Amsterdam Chapter 12, pp 309-339
    • (1996) Biochemistry of Lipids, Lipoproteins and Membranes
    • Merrill Jr., A.H.1    Sweeley, C.C.2
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    • For reviews on the synthesis of sphingosines:
    • For reviews on the synthesis of sphingosines:. Koskinen P.M., and Koskinen A.M.P. Synthesis (1998) 1075-1091
    • (1998) Synthesis , pp. 1075-1091
    • Koskinen, P.M.1    Koskinen, A.M.P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.