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1
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For reviews of the Prins reaction, see: a
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For reviews of the Prins reaction, see: a) E. Arundale, L. A. Mikeska, Chem. Rev. 1952, 51, 505.
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Arundale, E.1
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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.
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See also: d
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See also: d) G. W. Kabalka, Z. Wu, Y. Ju, Org. Lett. 2002, 4, 3415.
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0001673091
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ed. by B. M. Trost, I. Fleming, C. H. Heathcock, Pergamon, New York
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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.
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22
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0025863725
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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
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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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