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Supplementary data
Chem., Int. Ed. 2009, 48, 2225–2227.
6. Pedduri, Y.; Williamson, J. S. Tetrahedron Lett. 2008, 49, 6009–6012.
Experimental procedures and spectral data for compounds 3a–
g. X-ray crystal structure determination for (E)-3a. Supplementary
data associated with this article can be found, in the online version,
7. For
a review on the synthesis of methylenetetrahydrofurans by [3+2]
annulations see: Yamazaki, S. Chem. Eur. J. 2008, 14, 6026–6036.
8. (a) Fleury-Brégeot, N.; Jean, L.; Retailleau, P.; Marinetti, A. Tetrahedron 2007, 63,
11920–11927; (b) Panossian, A.; Fleury-Brégeot, N.; Marinetti, A. Eur. J. Org.
Chem. 2008, 3826–3833.
9. A 10 mol % amount of tributylphosphine (50
lL, 1 M solution in toluene) was
added to a solution of methyl 4-hydroxybut-2-ynoate (57 mg, 0.5 mmol) and N-
tosylimine 2a (0.5 mmol) in anhydrous CH2Cl2 (2 mL) under argon atmosphere.
The resulting mixture was stirred at room temperature for 24 h and the solvents
were removed. The crude product was purified by TLC on silica gel plates
(heptane/ethyl acetate, 7/3 mixture) to give the pure Z- and E-isomers of the final
oxazolidine 3a. No defined by-products have been isolated from these reactions.
10. Compounds (E)-3a and (Z)-3a were separated by TLC on silica gel with a heptane/
ethyl acetate 7/3 mixture as the eluent. (E)-3a: Rf = 0.33; white solid (mp = 117–
120 °C); 1H NMR (300 MHz, CDCl3) d 2.45 (s, 3H), 3.69 (s, 3H), 4.94 (dd,
J = 15.6 Hz, J = 1.8 Hz, 1H), 4.99 (dd, J = 15.6 Hz, J = 1.8 Hz, 1H), 6.11 (t,
J = 1.8 Hz, 1H), 6.53 (s, 1H), 7.30 (d, J = 8.4 Hz, 2H), 7.35–7.42 (m, 3H), 7.43–
7.50 (m, 2H), 7.64 (d, J = 8.4 Hz, 2H); 13C NMR (75 MHz, CDCl3) d 21.8, 51.5,
70.9, 94.2, 95.9, 127.0, 127.7, 128.8, 129.6, 130.1, 134.7, 137.3, 145.5, 151.5,
167.5 ppm. Anal. Calcd for C19H19NO5S: C, 61.11; H, 5.13; N, 3.75. Found: C,
61.17; H, 5.07; N, 3.51. (Z)-3a. Rf = 0.22; colorless oil; 1H NMR (300 MHz,
CDCl3) d 2.47 (s, 3H), 3.87 (s, 3H), 4.15 (d, J = 13.5 Hz, 1H), 4.19 (d, J = 13.5 Hz,
1H), 5.58 (s, 1H), 6.52 (s, 1H), 7.30–7.40 (m, 5H), 7.53 (d, J = 8 Hz, 2H), 7.79 (d,
J = 8 Hz, 2H); 13C NMR (75 MHz, CDCl3) d 21.8, 52.1, 68.2, 94.1, 106.6, 126.7,
128.1, 128.8, 129.3, 130.0, 135.1, 136.8, 144.1, 145.1, 166.0 ppm.
11. (a) David, O.; Vanucci-Bacqué, C.; Fargeau-Bellassoued, M.-C.; Lhommet, G.
Heterocycles 2004, 62, 839–846; (b) Tejedor, D.; González-Cruz, D.; García-
Tellado, F.; Marrero-Tellado, J. J.; Lopez Rodríguez, M. J. Am. Chem. Soc. 2004,
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Marrero-Tellado, J. J.; García-Tellado, F. J. Org. Chem. 2005, 70, 1042–1045.
12. (a) Junge, K.; Hagemann, B.; Enthaler, S.; Spannenberg, A.; Michalik, M.;
Oehme, G.; Monsees, A.; Riermeier, T.; Beller, M. Tetrahedron: Asymmetry 2004,
15, 2621–2631; For uses of t-Bu-Binepine as chiral organocatalyst, see: (b)
Wilson, J. E.; Fu, G. C. Angew. Chem., Int. Ed. 2006, 45, 1426–1429; (c) Wurz, R.
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