A tritylated cycloadduct (8-aza-1,4-oxidobicyclo[4.3.0]non-2-ene) was synthesized by reaction of N-allylfurfurylamine  with triphenylchloromethane followed by heating under reflux in toluene. The triphenyl group acted as a steric buttress enhancing the intramolecular Diels-Alder cycloaddition reaction of the N-allylfurfuryl amine. After its removal, 8-aza-1,4-oxidobicyclo[4.3.0]non-2-ene was isolated. Addition reactions were done on the double bond before deprotection, thus forming new compounds.

Synthesis of a Diels-Alder cycloadduct, 8-aza-1,4-oxidobicyclo[4.3.0]non-2-ene: Using trityl chloride as a steric buttress

243rd National Meeting (2012)

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