Dihydronaphthofuran skeletons can be found in various pharmaceutical and natural products used in treatments. Friedel-Crafts/substitution domino type reactions are practical for synthesizing these molecules. Applications of these reactions in domino type reactions are a trending topic in organocatalytic studies in the recent years. In the present study, it was chosen as the key step in domino reaction to afford disubstituted dihydronaphthofuran derivatives possessing two chiral centers in enantiomerically enriched forms. For this purpose, (Z)-(2-bromo-2-nitrovinyl)benzene and α or β–naphthol were used to perform model organocatalytic Friedel-Crafts/substitution domino type reaction (Scheme 1). Initial studies involve the screening of 2-aminoDMAP based and quinine based bifunctional organocatalysts. After choosing the proper sterically bulked (tert-butyl, 1-adamantyl, 2-adamantyl substituted) squaramide derived quinine based organocatalyst (Figure 1), the reaction conditions were optimized and getting the product in a very short duration (25 minutes) with 99% ee. The derivatization study was performed under the optimized condition.

Evaluation of the bifunctional organocatalysts in Friedel-Crafts/substitution domino type reaction

252nd National Meeting (2016)

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