Steric buttresses can be used to enhance certain Diels-Alder cycloaddition reactions which otherwise do not occur. Trityl chloride is bulky enough to be used as a steric buttress to perform an intra-molecular Diels-Alder reaction involving a furan ring system with an allyl or butenyl group. After the cycloaddtion, several addition reactions can be performed on the double bond of the cycloadduct before removing the buttress, thus making a library of novel compounds.

Using a steric buttress to enhance Diels-Alder cycloaddition reactions

245th National Meeting (2013)

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