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For an exhaustive revision on cyclization methodologies to prepare bicyclic β-lactams, see: (a) Kant, J.; Walker, D. G. In The Organic Chemistry of β-lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993 Chapter 3. Recent examples on the application of cyclization reactions to trinem and trinem derivatives synthesis: (b) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (d) Di Fabio, R.; Rossi, T.; Thomas, R. J.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (e) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (f) Rossi, T.; Marchiro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (d) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (e) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (f) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884.
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The cis-selectivity observed for compounds 1a,b, 2, and 11a-d was expected according to the current model for the Staüdinger reaction, (a) Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085. (b) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784. (c) Palomo, C.; Aizpurua, J. M.; Mielgo, A.; Linden, A. J. Org. Chem. 1996, 61, 9186. This model accounts for a 3R,4S stereochemistry for D-glyceraldehyde-derived 2-azetidinones. For an experimental study on the synthesis of 2-azetidinones derived from D- and L-glyceraldehyde acetonide imines, see: (d) Hubschwerelen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (e) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (f) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227 and references therein.
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The cis-selectivity observed for compounds 1a,b, 2, and 11a-d was expected according to the current model for the Staüdinger reaction, (a) Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085. (b) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784. (c) Palomo, C.; Aizpurua, J. M.; Mielgo, A.; Linden, A. J. Org. Chem. 1996, 61, 9186. This model accounts for a 3R,4S stereochemistry for D-glyceraldehyde-derived 2-azetidinones. For an experimental study on the synthesis of 2-azetidinones derived from D- and L-glyceraldehyde acetonide imines, see: (d) Hubschwerelen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (e) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (f) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227 and references therein.
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The cis-selectivity observed for compounds 1a,b, 2, and 11a-d was expected according to the current model for the Staüdinger reaction, (a) Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085. (b) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784. (c) Palomo, C.; Aizpurua, J. M.; Mielgo, A.; Linden, A. J. Org. Chem. 1996, 61, 9186. This model accounts for a 3R,4S stereochemistry for D-glyceraldehyde-derived 2-azetidinones. For an experimental study on the synthesis of 2-azetidinones derived from D- and L-glyceraldehyde acetonide imines, see: (d) Hubschwerelen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (e) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (f) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227 and references therein.
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The cis-selectivity observed for compounds 1a,b, 2, and 11a-d was expected according to the current model for the Staüdinger reaction, (a) Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085. (b) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784. (c) Palomo, C.; Aizpurua, J. M.; Mielgo, A.; Linden, A. J. Org. Chem. 1996, 61, 9186. This model accounts for a 3R,4S stereochemistry for D-glyceraldehyde-derived 2-azetidinones. For an experimental study on the synthesis of 2-azetidinones derived from D- and L-glyceraldehyde acetonide imines, see: (d) Hubschwerelen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (e) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (f) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227 and references therein.
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6 complexes can be isolated and characterized. See the Supporting Information for one example.
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56
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0001297245
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Examples: (a) Clive, D. L. J.; Cole, D. C.; Tao, Y. J. Org. Chem. 1994, 59, 1396-1406. (b) Chung, Y. K.; Lee, B. Y.; Jeong, N.; Hudecek, M.; Pauson, P. L. Organometallics 1993, 12, 220-223.
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Examples: (a) Clive, D. L. J.; Cole, D. C.; Tao, Y. J. Org. Chem. 1994, 59, 1396-1406. (b) Chung, Y. K.; Lee, B. Y.; Jeong, N.; Hudecek, M.; Pauson, P. L. Organometallics 1993, 12, 220-223.
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(a) DMSO: Chung, Y. K.; Lee, B. Y.; Jeong, N.; Hudecek, M.; Pauson, P. L. Organometallics 1993, 12, 220.
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61
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15144348595
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note
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1H NMR spectra of the crude reaction mixtures before purification.
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62
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(a) Smit, W. D.; Kireev, S. L.; Nefedov, O. M.; Tarasov, V. A. Tetrahedron Lett. 1989, 30, 4021-4024.
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For clarity through this work tricyclic systems has been numbered according with the numeration used for trinems. Thus, the four-membered ring nitrogen has been assigned the locator 1 and the remaining positions have been numbered to place the higher number on the carbonyl group (for 2-azetidinones) or former carbonyl carbon (for azetidines).
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Full spectroscopic and analytical data for compounds not included in this Experimental Section are described in the Supporting Information.
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