An efficient organocatalytic method for the asymmetric preparation of benzopyran‐ and benzofuran‐fused polycyclic acetals is described for the first time. This useful approach includes an interesting tunable Michael–acetalization of nitrostyrenes or α‐aromatization–acetalization of quinones. Under mild conditions, simple cyclic hemiacetals could be stereoselectively converted into four different types of polyheterocycles that serve as scaffolds for a number of bioactive natural products.magnified image
An efficient aminocatalytic enantioselective Michael addition of readily available cyclic hemiacetals to nitroolefins has been developed. The strategy serves as a powerful approach to synthetically valuable chiral 3-substituted tetrahydrofurans (THFs) and tetrahydropyrans (THPs). The synthetic utilities of the versatile Michael adducts also have been demonstrated in the synthesis of 2,3-disubstituted cyclic ethers, α-substituted lactones and venlafaxine analogues.
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