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Volumn 8, Issue 11, 2006, Pages 2405-2408

Enantioselective one-pot three-component synthesis of propargylamines

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EID: 33745697773     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060793f     Document Type: Article
Times cited : (216)

References (40)
  • 5
  • 34
    • 0029066475 scopus 로고
    • For a review on the π-stacking effect in asymmetric synthesis, see: (a) Jones, G. B.; Chapman, B. J. Synthesis 1995, 475.
    • (1995) Synthesis , pp. 475
    • Jones, G.B.1    Chapman, B.J.2
  • 36
    • 12344274699 scopus 로고    scopus 로고
    • The chiral ligand 1b has also been used for other enantioselective reactions. For references, see: (a) Lu, J.; Ji, S.-J.; Teo, Y.-C.; Loh, T.-P. Org. Lett. 2005, 7, 159.
    • (2005) Org. Lett. , vol.7 , pp. 159
    • Lu, J.1    Ji, S.-J.2    Teo, Y.-C.3    Loh, T.-P.4
  • 40
    • 33745730263 scopus 로고    scopus 로고
    • note
    • 6 (0.010 mmol, 5 mol %) in dry chloroform (2 mL) was stirred at room temperature for 30 min. An aldehyde (0.20 mmol) and an aromatic amine (0.20 mmol) were added, and the whole mixture was stirred for an additional 15 min at the same temperature. The reaction mixture was cooled to 0 °C, and an alkyne (0.30 mmol) was added. The reaction mixture was allowed to warm to 20-25 °C. After completion of the reaction (monitoring by TLC), the mixture was concentrated in vacuo and purified over silica gel by column chromatography (2-10% EtOAc in hexane) yielding pure propargylamine.


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