The Intramolecular Diels-Alder Reaction Reactivity and Stereocontrol

The Intramolecular Diels-Alder Reaction Reactivity and Stereocontrol 

Chapter One covers the range of dienes and dienophiles that have been used in the intramolecular Diels-Alder reaction, with some comments about the methods by which they can be prepared. This chapter addresses two other areas of interest the factors that govern the rate of the intramolecular Diels-Alder reaction, and, in reactions leading to the formation of one or more new chiral centers, the factors that govern the stereochemical outcome of the cyclization. 

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Boeckman et al. used an acetal tether in a racemic synthesis of the cyclohexene subunit of tetronolide 33 [16], Although it had previously been recognized that a Diels-Alder strategy could provide rapid entry into this highly functionalized six-mem-bered ring, some of the earlier reported intermolecular reactions suffered from relatively poor reactivity and regio- and stereocontrol [17]. It was anticipated that an intramolecular variant would overcome some of these problems (Scheme 10-10). 

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