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Volumn 36, Issue 1, 2007, Pages 12-13

Aza-prins reaction promoted by titanium tetraiodide and iodine

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EID: 34247210229     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2007.12     Document Type: Article
Times cited : (19)

References (23)
  • 1
    • 2642675659 scopus 로고
    • For reviews of the Prins reaction, see: a
    • For reviews of the Prins reaction, see: a) E. Arundale, L. A. Mikeska, Chem. Rev. 1952, 51, 505.
    • (1952) Chem. Rev , vol.51 , pp. 505
    • Arundale, E.1    Mikeska, L.A.2
  • 3
    • 0001290261 scopus 로고
    • ed. by B. M. Trost, I. Fleming, C. H. Heathcock, Pergamon, New York
    • c) B. B. Snider, in Comprehensive Organic Synthesis, ed. by B. M. Trost, I. Fleming, C. H. Heathcock, Pergamon, New York, 1991, Vol. 2, pp. 527-561.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 527-561
    • Snider, B.B.1
  • 6
    • 0001673091 scopus 로고
    • ed. by B. M. Trost, I. Fleming, C. H. Heathcock, Pergamon, New York
    • a) H. Hiemstra, W. N. Speckamp, in Comprehensive Organic Synthesis, ed. by B. M. Trost, I. Fleming, C. H. Heathcock, Pergamon, New York, 1991, Vol. 2, pp. 1047-1081.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 1047-1081
    • Hiemstra, H.1    Speckamp, W.N.2
  • 22
    • 0025863725 scopus 로고    scopus 로고
    • A typical procedure is as follows: Under an argon atmosphere, to a suspension of TiI4 (Soekawa Chemical Co, used after sublimation 278 mg, 0.50 mmol) and I2 (152mg, 0.60 mmol) in CH2Cl 2 (l.0 mL) were added simultaneously solutions of the imine 1 (51.8 mg, 0.20 mmol) in CH2C12 (l.0 mL) and phenylacetylene (61.3 mg, 0.60 mmol) in CH2Cl2 (l.0 mL) at rt during 3h using a microfeeder. After stirring at rt for 2h, the mixture was quenched by the addition of sat. NaHCO3 (aq) and NaHSO3 (aq, 5, The mixture was filtered through a Celite pad. The layers were separated and the aqueous layer was extracted with EtOAc (3 × 10 mL, The combined organic extracts were washed with sat. NaHCO3 (aq) and brine, and then dried over anhydous Na2SO4. Purification on silica gel TLC (Hexane/PhMe/AcOEt, 2/2/1) gave the adducts (Z)-7 49.1
    • 3) δ 13.9, 21.5, 55.8, 62.7, 103.0, 127.2, 128.3, 128.5, 128.9, 129.6, 135.1, 136.7, 140.3, 143.7, 168.6. For the assignment of the olefin geometries, see: D. P. Curran, D. Kim, Tetrahedron 1991, 47, 6171;


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