Diels-Alder oligomerization

Kohnke F. H., Mathias J. P., Stoddart J. F. Substrate-Directed Synthesis the Rapid Assembly of Novel MacropolycycUc Structures Via Stereoregular Diels-Alder Oligomerizations Top. Curr. Chem. 1993 165 1 69... 

Kohnke, F.H., Mathias, J.P., and Stoddart, J.F. Substrate-Directed Synthesis The Rapid Assembly of Novel Macropolycyclic Structures via Stereoregular Diels-Alder Oligomerizations. 165, 1-69 (1993). 

Assembly of Novel Macropolycyclic Structures via Stereoregular Diels-Alder Oligomerizations. 165, 1-69 (1993). 

Substrate-Directed Synthesis The Rapid Assembly of Novel Macropolycydic Structures via Stereoregular DIels-Alder Oligomerizations... 

Fig. 5. Schematic representation illustrating the basic premise of the repetitive Diels-Alder oligomerization process [21]. The macropolycyclization occurs as a consequence of the reaction between bisdiene and bisdienophilic building blocks whose relative stereochemistries and stereoelectronic characteristics dictate the structural outcome of the reaction...

Table 1. A comparison of the H NMR chemical shift data for structurally-related hydrogen atoms located on the Diels-Alder oligomerization adducts, provides a means by which their structural similarities and differences may be highlighted. The alphabetic descriptors correspond to those included in the Schemes outlining the syntheses of these compounds...

In summary, the success of the trebly diastereoselective repetitive Diels-Alder oligomerization process for the synthesis of outwardly complex molecular structu-... 

Another example of a repetitive methodology is the stereoregular Diels-Alder oligomerization procedure reported in 1992 by Stoddart et al.7 (Scheme 4). With this molecular LEGO strategy, he built several cycloacenes by periodical repetition of the same procedures. 

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