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Chiral auxiliaries in cycloadditions by Karola Rück-Braun, Horst Kunz

By Karola Rück-Braun, Horst Kunz

Because the days of Diels, Alder and Woodward, cycloadditions were one of the such a lot flexible reactions for stereoselective synthesis ... All appropriate details is gathered during this well-structured, sensible instruction manual. prepared in line with the cycloaddition kind, the right auxiliaries, reactants, stereoselectivities, yields, and references for every key response are compiled in compact tables. Scientists attracted to the theoretical heritage of stereoselective cycloadditions will locate a good number of in-depth literature references. ... with this finished information assortment cycloadditions becomes an excellent extra robust instrument for each natural chemist engaged on stereoselective synthesis.

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Extra info for Chiral auxiliaries in cycloadditions

Example text

In particular, the molecular cell complexes of both of these molecules are topologically chiral. Chemically, [nlparacyclophane and triple layered cyclophane are chiral. both [m] Figure 32. Planar presentations of the graphs of [m][n]paracyclophane and triplelayered cyclophane. These are not the only examples of molecules whose graphs are topologically planar, yet whose cell complexes contain a 3-rung Mobius ladder. The examples given above, as well as other similar examples, show that a molecular graph may be topologically achiral, while the corresponding molecular cell complex is topologically chiral and the molecule itself is chiral.

In order to illustrate this definition, consider the 4-rung Mobius ladder with numbered vertices, which is illustrated in Figure 38. There exists an automorphism of the 4-rung Mobius ladder that sends each numbered vertex to the position of the preceding numbered vertex, because this operation preserves adjacency of vertices. If we perform this automorphism on the embedded Mobius ladder of Figure 38, the vertices will be rearranged as illustrated in Figure 39. 32 2 A Knot Theoretic Approach To Molecular Chirality I Figure 39.

Consider the molecular graph of the ferrocenophane derivative illustrated on the left side of Figure 35. We saw in Figure 36 that this graph contains a Mobius ladder with four rungs. By omitting one rung, the graph contains a Mobius ladder with three rungs. However, we cannot use the method of the previous section to show that this graph is intrinsically chiral because a deformation of the ferrocenophane graph to its mirror image will not create a deformation of a 3-rung Mobius ladder to its mirror image.

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