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Organocatalytic Asymmetric Addition of Aromatic α‑Cyanoketones to o‑Quinone Methides: Synthesis of 3,4-Dihydrocoumarins and Tetrasubstituted Chromans

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journal contribution
posted on 31.08.2021, 20:08 by Chandan Gharui, Chandrakanta Parida, Subhas Chandra Pan
The first organocatalytic asymmetric addition of aromatic α-cyanoketones to in situ-generated o-quinone methides has been developed. The products 3,4-dihydrocoumarin and tetrasubstituted chroman were obtained via addition of aromatic α-cyanoketones to in situ-generated o-quinone methides followed by treatment with 0.7 N HCl. With 10 mol % catalyst, the desired products were obtained in high enantio- and diastereoselectivities.

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