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Bifunctional Primary Amine-Squaramide Catalyzed Enantioselective Intramolecular Michael Addition of Keto-enones: A Convenient Process to the Stereocontrolled Construction of trans-Dihydrobenzofuran Skeletons
Bifunctional Primary Amine-Squaramide Catalyzed Enantioselective Intramolecular Michael Addition of Keto-enones: A Convenient Process to the Stereocontrolled Construction of trans-Dihydrobenzofuran Skeletons
A highly diasterero- and enantioselective intramolecular Michael addition of keto-enones has been realized. By using the (R,R)-1,2-diphenylethane-1,2-diamine-based bifunctional primary amine-squaramide catalyst, the reaction proceeded smoothly to generate the corresponding trans-2,3-disubstituted dihydrobenzofuran derivatives in excellent yields with good to excellent diastereo- and enantioselectivities (up to 97:3 dr, up to 99% ee).
