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I. O\u2019Donnel, Asymmetric Phase Transfer Reactions; in Catalytic Asymmetric Synthesis; I. Ojima, Ed.; VCH-Publishers, New York, 1993."},{"key":"#cr-split#-10.3987\/COM-00-9098-1.2","doi-asserted-by":"crossref","unstructured":"(b) A. Nelson, Angew. Chem., Int. Ed., 1999, 38, 1583.","DOI":"10.1002\/(SICI)1521-3773(19990601)38:11<1583::AID-ANIE1583>3.0.CO;2-E"},{"key":"#cr-split#-10.3987\/COM-00-9098-2.1","doi-asserted-by":"crossref","unstructured":"(a) E. V. Dehmlow, R. Klauck, S. D\u00fcttmann, B. Neumann, and H.-G. Stammler, Tetrahedron; Asymmetry, 1998, 9, 2235 .","DOI":"10.1016\/S0957-4166(98)00213-4"},{"key":"#cr-split#-10.3987\/COM-00-9098-2.10","doi-asserted-by":"crossref","unstructured":"(j) M. J. O\u2019Donnell, S. Wu, and J. C. Huffman, Tetrahedron, 1994, 50, 4507.","DOI":"10.1016\/S0040-4020(01)89382-0"},{"key":"#cr-split#-10.3987\/COM-00-9098-2.11","doi-asserted-by":"crossref","unstructured":"(k) S. Chang, J. M. Galvin, and E. N. Jacobsen, J. Am. Chem. Soc., 1994, 116, 6937.","DOI":"10.1021\/ja00094a059"},{"key":"#cr-split#-10.3987\/COM-00-9098-2.12","unstructured":"(l) G. MaCdonald, L. Alcaraz, N. J. Lewis, and R. J. K. Taylor, Tetrahedron Lett., 1998, 39, 5433."},{"key":"#cr-split#-10.3987\/COM-00-9098-2.13","doi-asserted-by":"crossref","unstructured":"(m) S. Arai, T. Ishida, and T. Shioiri, Tetrahedron Lett., 1998, 39, 8299.","DOI":"10.1016\/S0040-4039(98)01811-5"},{"key":"#cr-split#-10.3987\/COM-00-9098-2.14","doi-asserted-by":"crossref","unstructured":"(n) B. Lygo and P. G. Wainwright, Tetrahedron Lett., 1997, 38, 8595 .","DOI":"10.1016\/S0040-4039(97)10293-3"},{"key":"#cr-split#-10.3987\/COM-00-9098-2.15","doi-asserted-by":"crossref","unstructured":"(o) E. J. Corey, F. Xu, and M. C. Noe, J. Am. Chem. Soc., 1997, 119, 12414.","DOI":"10.1021\/ja973174y"},{"key":"#cr-split#-10.3987\/COM-00-9098-2.16","doi-asserted-by":"crossref","unstructured":"(p) M. J. O\u2019Donnell, F. Delgado, C. Hostettler, and R. 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Chem., 1996, 61, 3700.","DOI":"10.1021\/jo950969j"},{"key":"#cr-split#-10.3987\/COM-00-9098-5.3","doi-asserted-by":"crossref","unstructured":"(c) T. Itoh, S. Shirakami, Y. Nakao, and T. Yoshida, Chem. Lett. 1998, 979.","DOI":"10.1246\/cl.1998.979"},{"key":"#cr-split#-10.3987\/COM-00-9098-5.4","doi-asserted-by":"crossref","unstructured":"(d) S. Shirakami and T. Itoh, Tetrahedron: Asymm., 2000, 11, 2823.","DOI":"10.1016\/S0957-4166(00)00247-0"},{"key":"#cr-split#-10.3987\/COM-00-9098-5.5","doi-asserted-by":"crossref","unstructured":"(e) M. Takeuchi, T. Mizuno, S. Shinkai, S. Shirakami, and T. Itoh, Tetrahedron: Asymm., 2000, 11, 3311.","DOI":"10.1016\/S0957-4166(00)00307-4"},{"key":"10.3987\/COM-00-9098-6","unstructured":"6. T. V. RajanBabu, T. A. Ayers, G. A. Halliday, K. K. You, and J. C. Calabress, J. Org. Chem., 1997, 62, 6012."},{"key":"10.3987\/COM-00-9098-7","unstructured":"7. MacSpartan Pro was employed for MO (PM3) calculation. Results of MO (PM3) calculation (Heat of formation): 1a; -271.63 Kcal\/mol, 2a; -270.10 Kcal\/mol."},{"key":"10.3987\/COM-00-9098-8","doi-asserted-by":"crossref","unstructured":"8. M. J. Eis, and B. Ganem, Carbohydrate Res., 1988, 316.","DOI":"10.1016\/0008-6215(88)80144-7"},{"key":"10.3987\/COM-00-9098-9","doi-asserted-by":"crossref","unstructured":"9. P. D. Cesare, and B. Gross, Synthesis, 1979, 458.","DOI":"10.1055\/s-1979-28719"},{"key":"10.3987\/COM-00-9098-10","unstructured":"10. Physical constant and NMR data of 2b: colorless syrup; Rf 0.46 (CHCl3 \/ MeOH = 3:1); [\u03b1]D23 +28.4\u00b0 (c1.38, CHCl3); 1H NMR (200 MHz, \u03b4, CDCl3) 0.90 (3H, t, J=7.3 Hz), 1.26-1.68 (4H, m), 1.97 (1H, br s), 2.68-2.92 (4H, m), 3.33 (3H, s), 3.28-4.16 (20H, m), 4.56 (1H, d, J=3.5 Hz), 4.61 (1H, d, J=12.2 Hz), 4.73 (1H, d, J= 12.2 Hz), 7.27-7.33 (5H, m); 13C NMR (50 MHz, ppm, CDCl3) 13.9, 19.3, 31.7, 47.5, 47.9, 55.0, 69.1, 69.4, 69.6, 69.8, 70.0, 70.4, 71.4, 72.6, 73.1, 73.2, 80.0, 81.4, 98.1, 127.9, 128.0, 128.4, 138.1; IR (neat, cm-1) 3384, 2921, 1459, and 1100. 3b: colorless solid; mp 76-78\u00c5\u00e3C (recrystallization from CHCl3); Rf 0.48 (CH2Cl2 \/ MeOH = 3:1); [\u03b1]D29 +70.3\u00b0 (c 0.76, CHCl3); 1H NMR (200 MHz, \u03b4, CDCl3) 0.91 (6H, t, J= 7.3 Hz), 1.26-1.63 (8H, m), 2.33 (1H, br s), 2.83-2.86 (4H, m), 3.12-4.10 (22H, m), 3.40 (3H, s), 4.78 (1H, d, J= 3.5 Hz); 13C NMR (50 MHz, ppm, CDCl3) 13.8, 13.9, 19.1, 19.3, 32.1, 32.6, 48.4, 55.0, 69.2, 69.8, 70.4, 70.8, 71.2, 71.3, 72.2, 72.3, 73.1, 78.6, 80.8, 81.6, 97.7; IR (neat, cm-1) 3333, 2923, 1462, 1365, 1106, and 796. Michael adduct (15): colorless syrup; Rf 0.23 (hexane \/ ethyl acetate = 2:1); [\u03b1]D23 -47.9\u00b0 (c 1.15, CHCl3), 72%ee(S); 1H NMR (200 MHz, \u03b4, CDCl3) 1.43 (9H, s), 2.11(3H, s), 2.15 (2H, t, J= 7.3 Hz), 2.52 (2H, dt, J= 7.3, 6.1 Hz), 3.95 (1H, t, J= 6.1 Hz), 7.13-7.64 (10H, m); 13C NMR (50 MHz, ppm, CDCl3) 27.7, 28.0, 29.9, 39.8, 64.7, 77.2, 81.1, 127.7, 128.0, 128.4, 128.6, 128.7, 130.3, 136.4, 139.4, 170.5, 170.9, 208.3; IR (neat, cm-1) 3060, 2974, 1728, 1710, 1627, and 1154."}],"container-title":["HETEROCYCLES"],"original-title":[],"language":"en","deposited":{"date-parts":[[2024,6,24]],"date-time":"2024-06-24T20:31:23Z","timestamp":1719261083000},"score":1,"resource":{"primary":{"URL":"https:\/\/triggered.stanford.clockss.org\/ServeContent?doi=10.3987%2Fcom-00-9098"},"secondary":[{"URL":"https:\/\/triggered.edinburgh.clockss.org\/ServeContent?doi=10.3987%2Fcom-00-9098","label":"edinburgh"}]},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2001]]},"references-count":47,"journal-issue":{"issue":"1","published-print":{"date-parts":[[2001]]}},"alternative-id":["COM-00-9098"],"URL":"https:\/\/doi.org\/10.3987\/com-00-9098","relation":{},"ISSN":["0385-5414"],"issn-type":[{"type":"print","value":"0385-5414"}],"subject":[],"published":{"date-parts":[[2001]]}}}