Ring-selective synthesis of O-heterocycles from acyclic 3-O-allyl-monosaccharides via intramolecular nitrone-alkene cycloaddition

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Abstract

Intramolecular 1,3-dipolar cycloadditions of nitrones formed from 3-O-allyl-D-glucose and D-altrose (both with threo-configuration at C-2,3) afford oxepanes selectively whereas the same reactions of nitrones derived from 3-O-allyl-D-allose and D-mannose (both with erythro-configuration at C-2,3) give tetrahydropyrans selectively. © 2001 Elsevier Science Ltd.

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Shing, T. K. M., & Zhong, Y. L. (2001). Ring-selective synthesis of O-heterocycles from acyclic 3-O-allyl-monosaccharides via intramolecular nitrone-alkene cycloaddition. Tetrahedron, 57(8), 1573–1579. https://doi.org/10.1016/S0040-4020(00)01138-8

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