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22844434551
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note
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3N
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20
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22844450195
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note
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13C NMR and IR Spectroscopy.
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21
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0028941858
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For another example of an amide cyclization onto a π-allylpalladium complex, see: Hansel, J.-G.; O'Hogan, S.; Lensky, S.; Ritter, A. R., Miller, M. J. Tetrahedron Lett. 1995, 36, 2913.
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22
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22844434124
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note
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3N
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-
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23
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22844440086
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The cyclization of amides onto double bonds activated by sulphenylation has been limited to aryl amides as alkyl amides gave low (10%) yields. See ref 3a and Abd El Samii, Z. K. M.; Al Ashmay, M. I.; Mellor, J. M. Tetrahedron Lett. 1987, 28, 1929.
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22844451274
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note
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AB INITIO calculations (Spartan) for the alanine derived oxazoline gave trans:cis ratios of 5.7:1 (STO-3G) and 6.7:1 (630G).
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-
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25
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0000674932
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Palladium π-allyl complexes are known to undergo inversion. For mechanistic discussions, see: (a) Bäckvall, J.-E.; Granberg, K. L. J. Am. Chem. Soc. 1992, 114, 6858.
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22844447747
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note
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Good diastereoselectivity with serinal derivatives has been particularly problematic. See refs. 5b and 5c.
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-
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28
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0025250109
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1H NMR chemical shifts of the ring protons (0.3 to 0.5 ppm upfield shift for trans relative to cis) in analogy to the reported oxazolidinones. Sakaitani, M.; Ohfune, Y. J. Am. Chem. Soc. 1990, 112, 1150.
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