Abstract

Novel sulfonamide organocatalysts were prepared from chiral Betti base and various sulfonyl chlorides, and applied to the asymmetric hetero-Diels-Alder reaction of ethyl glyoxylate with Danishefsky's diene. The sulfonamides exhibited catalytic activity as hydrogen bond donor. In particular, sulfonamide 3g showed highest catalytic performance for the reaction. Sulfonamide 3g catalyzed asymmetric reaction followed by treatment with TFA obtained corresponding 6-substituted 2,3-dihydropyran-4-ones in moderate yield and enantioselectivity.

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