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16.21: Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
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Organic Chemistry

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Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
 
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16.21: Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.

Figure1

Dienophiles with one or more electron-withdrawing substituents form stereochemically different products in which the substituents are oriented in an endo (towards) or exo (away) configuration relative to the double bond.

Figure2

The endo isomer is formed faster and is the kinetic product. The exo isomer is more stable and is the thermodynamic product.

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