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.
Chandan Gharui, Chandrakanta Parida, Subhas Chandra Pan. Organocatalytic Asymmetric Addition of Aromatic α-Cyanoketones to o-Quinone Methides: Synthesis of 3,4-Dihydrocoumarins and Tetrasubstituted Chromans. The Journal of organic chemistry. 2021 Sep 17;86(18):13071-13081
PMID: 34464133
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