Graduate Thesis Or Dissertation
 

The use of the Diels-Alder reaction in asymmetric synthesis

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  • The Diels-Alder reaction represents a promising tool for use in asymmetric synthesis. The reaction involves a rigid transition state that facilitates the formation of one diastereomeric transition state and is reversible. This satisfies two necessary criteria for asymmetric synthesis. The Diels-Alder reactions of 1,l-dialkylspiro[2.4]-4,6- heptadienes with maleic anhydride and p-benzoquinone in chloroform were studied. The spirodienes were generated by the reactions of 6,6- dialkylfulvenes with dimethyloxosulfonium methylide in dimethyl sulfoxide. Complete facial differentiation of cis-9-tert-butyldispiro[ 4.0.5.1]-1,3-dodecadiene was found in its Diels-Alder reactions with maleic anhydride and p-benzoquinone. Less complete facial differentiation was effected with 1,l-dimethylspiro[2.4]-4,6- heptadiene and dispiro-[4.0.5.1]-1,3-dodecadiene. The Diels-Alder reaction of p-benzoquinone and spiro[2.4]-4,6-heptadiene was found to be reversible at 170°.
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