Tricyclic heterocycles as precursors to functionalized spirocyclic oximes |
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Authors: | Silas A Griffin Cody R Drisko Kevin S Huang |
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Institution: | Department of Biology and Chemistry, Azusa Pacific University, 901 E. Alosta Ave., Azusa 91702-7000, USA |
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Abstract: | An efficient synthesis of functionalized spirocyclic oximes from tricyclic heterocycles is reported. This novel method accomplishes high diastereoselectivity via an intramolecular 1,3-dipolar cycloaddition with a regenerating Michael linker strategy. Ring opening of the tricyclic N-(trimethylsilyloxy)pyrrolo3,4-c]isoxazolidine framework was found to be essential for successful N-alkylation of the tertiary amine on the polymer support. β-Elimination of the quaternary salt releases the spirocyclic oximes from the solid support in overall yields of 45–60%. |
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Keywords: | Spirocyclic oximes Regenerating Michael linker Solid-phase synthesis Intramolecular 1 3-dipolar cycloaddition |
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