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For the preparation and characterization of catalyst la, see: (a) Nguyen, S. T.; Johnson, L. K.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1992, 114, 3974-3975.
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For the preparation and characterization of catalyst 1b, see: (c) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110.
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33847488366
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13C NMR, IR, and mass spectral characteristics (see Experimetal Section). The cases involving C-allylglycine in Scheme 1 were performed on the racemic mixtures
-
13C NMR, IR, and mass spectral characteristics (see Experimetal Section). The cases involving C-allylglycine in Scheme 1 were performed on the racemic mixtures.
-
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39
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33847474941
-
-
We have discussed this issue in more detail in ref 2g
-
We have discussed this issue in more detail in ref 2g.
-
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40
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0001653694
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33646951660
-
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note
-
A monocyclized product was identified by FABMS. No ions corresponding to the bicyclization product could be detected. The monocyclized product was formed at approximately the same rate as the six-membered cyclic product 5, and no other product was formed after elongated reaction time. The formation of cyclic product 5 was previously found to be fast and effectively irreversible. Thus, we believe that treatment of substrate 10 under the analogous reaction conditions leads to the sixmembered monocyclization product as opposed to the 11-membered monocyclization product.
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43
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The disulfide dihedral angle in 10 has been shown to be 82° with right-handed chirality in the solid state. Ravi. A.; Prasad, B. V.; Balaram, P. J. Am. Chem. Soc. 1983, 105, 105-109.
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33847487057
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A related cyclization was performed with unprotected tyrosine which afforded the analogous macrocycle in 70% yield. The free phenol therefore does not interfere with catalyst activity
-
A related cyclization was performed with unprotected tyrosine which afforded the analogous macrocycle in 70% yield. The free phenol therefore does not interfere with catalyst activity.
-
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54
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0000802654
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See ref 19
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See ref 19.
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See ref 18
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See ref 18.
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60
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-
33847454208
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The olefin geometry of 22 was not assigned
-
The olefin geometry of 22 was not assigned.
-
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61
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33847453823
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1H NMR. This impurity is not present in the cyclized product 16
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1H NMR. This impurity is not present in the cyclized product 16.
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