A mild One-Step Procedure for the Synthesis of β-Iodo Epoxides from the Corresponding Epoxy-Alcohols

References

• Mori , K. and Ebata , T. 1981 . Tetrahedron Lett. , 22 : 4281
   Google Scholar
• Nicolaou , K. C. , Duggan , M. E. and Ladduwahetty , T. 1984 . Tetrahedron Lett. , 25 : 2069
   Google Scholar
• Millar , J. G. and Underhill , E. W. 1986 . J. Org. Chem. , 51 : 4726
   Google Scholar
• Hwang , C. K. , Li , W. S. and Nicolaou , K. C. 1984 . Tetrahedron Lett. , 25 : 2295
   Web of Science ®Google Scholar
• Rollin , P. and Pougny , J. R. 1986 . Tetrahedron , 42 : 3490
   Google Scholar
• Pougny , J. R. and Rollin , P. 1987 . Tetrahedron Lett. , 28 : 2977
   Google Scholar
• Ho , P. T. and Davies , N. 1984 . J. Org. Chem. , 49 : 3027
   Web of Science ®Google Scholar
• Manna , S. , Falck , J. R. and Mioskowski , C. 1985 . Synth. Commun. , 15 : 663
   Web of Science ®Google Scholar
• Viaud , M. C. and Rollin , P. 1990 . Synthesis , : 130 and references cited.
   Web of Science ®Google Scholar
• Tanaka , S. , Yamamoto , H. , Nozaki , H. , Sharpless , K. B. , Michaelson , R. C. and Cutting , J. D. 1974 . J. Am. Chem. Soc. , 96 : 5254
   Google Scholar
• F = 49–50°C after recrystallization from Et2O + hexane; anal, calcd for CgHgIO (260.07) C% 41.56, H% 3.49; found C% 41.55, H% 3.50
   Google Scholar
• Pougny , J. R. and Rollin , P. 1986 . J. Carbohydr. Chem. , 5 : 701
   Web of Science ®Google Scholar
• Pougny , J. R. and Rollin , P. unpublished results.
   Google Scholar
• Morin , C. 1983 . J. Chem. Res, (S) , : 275 For a similar synthesis of the (3S,4S)-epimer of 1e from L-arabinose, see
   Google Scholar
• [α]D = -32° (c 1.96, CHCI3); complementary relevant 1H-NMR data δ 5.56 (1H, m, J6,5 = 10.5 Hz, H-6), 5.45 (1H, m, H-5), 2.34 (1H, m, H-4), 2.27 (1H, m, H-4′), 2.06 (2H, dt, H-7 & H-7′); HRMS calcd for C11H19IO 294.0482, obsd 294.0506.
   Google Scholar
• [α]D = -40° (c 1.80, CHCI3); 1H-NMR δ 5.25–5.65 (4H, m, olefinic protons), 2.82 (2H, m, H-7 & H-7′), 2.23–2.45 (2H, m, H-4 & H-4′), 1.97–2.15 (2H,m, H-10 & H-10′). HRMS calcd for C11H17IO 292.0326, obsd 292.0319.
   Google Scholar
• [α]D = -49° (c 2.49, CHCI3); 1H-NMR (arbitrary proton numbering) δ 3.69 (3H, s, COOMe), 2.42 (2H, 2dt, H-6 & H-6′), 1.87 (2H, m, H-5 & H-5′), 1.68 (1H, m, H-4), 1.48 (1H, m, H-4′); HRMS calcd for C8H13IO3 283.9911, obsd 283.9894.
   Google Scholar
• [α]D = -25° (c 1.56, CHGl3); 1H-NMR (arbitrary proton numbering) δ 4.01 (1H, dd, J5,4 = 8.3 Hz, J5,4- = 6.5 Hz, H-5), 2.12 (1H, ddd, Jgem = 14.7 Hz, j4,3 = 7.4 Hz, H-4), 1.96 (1HL ddd, J4′,3 = 4.7 Hz, H-4′); HRMS calcd for CgH17IOS2 331.9767, obsd 331.9778.
   Google Scholar
• Evans , R. D. , Magee , J. W. and Schauble , J. H. 1988 . Synthesis , : 862 and references cited.
   Google Scholar
• Xiao , X. , Park , S. K. and Prestwich , G. D. 1988 . J. Org. Chem. , 53 : 4869
   Web of Science ®Google Scholar