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| - Diastereoselective Synthesis of 2,3,5-TrisubstitutedTetrahydrofurans via Cyclofunctionalization Reactions. Evidenceof Stereoelectronic Effects
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| - The work described herein considers the impact of stereoelectronic effects and allylic 1,3-strain incontrolling the cyclofunctionalization reaction when a hydroxyl group is at the allylic position. Thestereoelectronic arguments are supported by independent iodocyclization reactions performed usingtwo secondary alcohols. The transition-state pathways involved in these reactions are establishedthrough a comparison of relative reaction rates. A bi-directional approach is used to demonstratethe potential of the iodocyclization reaction to differentiate a terminus in molecules with a pseudoC2 axis of symmetry, showing that two-directional synthesis can be used to differentiate betweenalternative transition-state pathways.
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