Steric buttresses can be used to enhance certain Diels-Alder cycloaddition reactions. Triphenylchloromethane (trityl chloride) is bulky enough to be used as a steric buttress to perform intra-molecular Diels-Alder cycloaddition reactions involving a furan ring system, reactions which otherwise do not occur. Three tritylated Diels-Alder cycloadducts were successfully made by reactions of their respective N-alkenylfurfurylamine with trityl chloride followed by heating under reflux with toluene. The trityl group acted as a steric buttress enhancing the Diels-Alder intramolecular cycloaddition reactions. This group was finally deprotected to form the cycloadducts: 8-aza-1,4-oxidobicyclo[4.3.0]non-2-ene (4a); 9-aza-1,4-oxidobicyclo[4.4.0]dec-2-ene (4b); and 10-aza-1,4-oxidobicyclo[5.4.0]undec-2-ene (4c). After the cycloaddtion, several addition reactions can be performed on the double bond of the cycloadduct before removing the buttress, as well as on the secondary amine after deprotection thus making a library of novel compounds.

Use of triphenylchloromethane (trityl chloride) as a steric buttress<br />
to enhance Diels Alder cycloaddition reactions

249th National Meeting (2015)

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Use of triphenylchloromethane (trityl chloride) as a steric buttress<br /> to enhance Diels Alder cycloaddition reactions