Reaction of Cyclic Sulfates with Phosphines

References

• Fischer , G. W. and Zimmermann , T. 1984 . “ Five-membered Rings containing Three Oxygen or Sulfur Atoms. In Comprehensive Heterocyclic Chemistry ” . Edited by: Potts , K. T. Vol. 5 , pp. 851 – 895 . Oxford : Pergamon Press .
   Google Scholar
• Turvey , J. R. 1965 . Advan. Carbohydr. Chem. , 20 : 209
   Google Scholar
• Hough , L. and Richardson , A. C. 1967 . “ Rodds Chemistry of Carbon Compounds ” . Edited by: Coffey , S. Vol 1F , pp. 419 – 422 . Amsterdam : Elsevier . 2nd ed.
   Google Scholar
• Gao , Y. and Sharpless , K. B. 1988 . J. Am. Chem. Soc. , 110 : 7538
   Web of Science ®Google Scholar
• Kim , B. M. and Sharpless , K. B. 1989 . Tetrahedron Lett. , 30 : 655
   Web of Science ®Google Scholar
• Lohray , B. B. , Gao , Y. and Sharpless , K. B. 1989 . Tetrahedron Lett. , 30 : 2623
   Web of Science ®Google Scholar
• Oi , R. and Sharpless , K. B. 1991 . Tetrahedron Lett. , 32 : 999
   Web of Science ®Google Scholar
• Block , E. 1984 . Organic Reactions , 30 : 457
   Google Scholar
• Corey , E. J. and Winter , R. A. E. 1963 . J. Am. Chem. Soc. , 85 : 2677
   Web of Science ®Google Scholar
• Compound 19: 1H NMR(300MHz, CDCl3) δ 0.81(t, J = 7.5Hz, 3H), 1.90(d, 2JP,H = 14.5Hz, 9H), 3.78–4.02(m, 2H), 4.61(dd, J = 3.7Hz, 2JP,H = 19.5Hz, 1H), 5.18(dd, J = 3.7Hz, 3JP,H = 3.1Hz, 1H), 7.4(brs, 5H); 13C NMR(CDCl3) δ 6.7(d, 1JP,C = 53Hz), 13.5, 42.9(d, 1JP,C = 51Hz), 60.5, 72.6(d, 2JP,C = 4Hz), 129.1, 129.3, 129.5, 129.6, 130.9, 131.0, 168.0(d, 2JP,C = 15Hz)
   Google Scholar
• 1H and 13C NMR spectra of 20 indicated that a mixture of diastereomeric salts was produced
   Google Scholar
• Compound 23: [α]D 24 +27.4°(c 0.05, H2O), lit.10 [α]D 20 + 29°(c, 3.2, H2O); 1H NMR(300MHz, CDCl3) δ 1.33(s, 3H), 1.51(s, 3H), 2.45(brs, 1H), 3.47(dd, 1H), 3.93(dd, 1H), 4.24–4.31(m, 1H), 4.50(d, J = 3.9Hz, 1H), 4.62(d, J = 3.6Hz, 1H), 4.77(t, 1H), 5.93(d, J = 3.6Hz, 1H); 13C NMR (CDCl3) δ 26.7, 27.4, 72.4, 72.5, 82.4, 85.1, 85.5, 107.0, 113.1
   Google Scholar
• Compound 24: 1H NMR(300MHz, CDCl3) δ 1.31(s, 3H), 1.47(s, 3H), 1.55(d, 2JP,H = 12.8Hz, 3H), 1.84(d, 2JP,H = 14.3Hz, 6H), 2.55(m,1H), 2.85 (m, 1H), 4.24(d, J = 3.6Hz,1H), 4.59(ABq, 2H), 4.61(d, J = 3.6Hz, 1H), 4.73(t, 1H), 4.95(m, 1H), 5.92(d, J = 3.6Hz, 1H), 7.31–7.35(m, 5H)
   Google Scholar
• Lewis , B. A. , Smith , F. and Stephen , A. M. 1963 . “ Methods in Carbohydrate Chemistry ” . Edited by: Whistler , R. L. , Wolfrom , M. L. and BeMiller , J. N. Vol II , pp. 182 – 183 . New York : Academic Press .
   Google Scholar
• Financial support from the Korea Science and Engineering Foundation and the Organic Chemistry Research Center is gratefully acknowledged
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