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(a) Seebach, D.; Abele, S.; Gademann, K.; Guichard, G.; Hintermann, T.; Jaun, B.; Matthews, J. L.; Schreiber, J. V.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1998, 81, 932.
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(b) 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.
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N-p-Methoxyphenylbenzaldimine was used, as it allows easy oxidative removal of the p-methoxyphenyl group, with ammonium cerium (IV) nitrate, to give the N-unsubstituted β-lactam, as shown in: Kronenthal, D. R.; Han, C. Y.; Taylor M. K. J. Org. Chem. 1982, 47, 2765.
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5444257295
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note
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3 (c 0.7), are +134.0 and -134.0, respectively.
-
-
-
-
26
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5444236252
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note
-
The relative stereochemistry of 15a (and therefore 15b) was studied by NMR (NOESY spectra), and was confirmed to be cis, thus excluding a possible epimerization of the carbon atom C3 (see Suporting Information).
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-
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27
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0025977155
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The racemic 4-formyl β-lactam, rac-15-cis was prepared according to a procedure previously described: (a) Alcaide, B.; Martín-Cantalejo, Y.; Plumet, J.; Rodríguez-López, J.; Sierra, M. A. Tetrahedron Lett. 1991, 32, 803.
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0004133516
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The program Gaussian 98 was used: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A. 11.3; Gaussian, Inc.: Pittsburgh, PA, 2002.
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Stratmann, R.E.9
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Dapprich, S.11
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Daniels, A.D.13
Kudin, K.N.14
Strain, M.C.15
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Clifford, S.24
Ochterski, J.25
Petersson, G.A.26
Ayala, P.Y.27
Cui, Q.28
Morokuma, K.29
Malick, D.K.30
Rabuck, A.D.31
Raghavachari, K.32
Foresman, J.B.33
Cioslowski, J.34
Ortiz, J.V.35
Stefanov, B.B.36
Liu, G.37
Liashenko, A.38
Piskorz, P.39
Komaromi, I.40
Gomperts, R.41
Martin, R.L.42
Fox, D.J.43
Keith, T.44
Al-Laham, M.A.45
Peng, C.Y.46
Nanayakkara, A.47
Gonzalez, C.48
Challacombe, M.49
Gill, P.M.W.50
Johnson, B.G.51
Chen, W.52
Wong, M.W.53
Andres, J.L.54
Head-Gordon, M.55
Replogle, E.S.56
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