An important variation of the DielsAlder reaction is intramolecular, in which the diene

Chapter 15, Problem 15-41

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An important variation of the DielsAlder reaction is intramolecular, in which the diene and the dienophile are connected. This type of DielsAlder reaction makes two new rings. Draw the compound produced in each of these examples; try to predict stereochemistry (using models will help). In some cases, Lewis acid catalysts are used; that can be ignored for this problem. (a) C N (b) O OSiR3 OR2 (c) O O O O SiMe3 (d) O O C CH Ar2 Ar1 Prof. A. Kirschning, Leibnitz U. Hannover Organic Letters, 2014, 16, 568. (Ar1 and Ar2 are different aryl groups.) Prof. H. Miyaoka, Tokyo U. Synthesis Letters, 2011, 547. (R and R2 are different alkyl groups.) Prof. H. Zhai, Lanzhou U. Organic Letters, 2014, 16, 216.

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