Stereoselective Synthesis of Cyclic Ether Compounds via Reductive Cleavage of Bicyclic Ketals
Stereoselective Synthesis of Cyclic Ether Compounds via Reductive Cleavage of Bicyclic Ketals

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Bicyclic ketals in the 6,8-dioxabicyclo[3.2.1]octane system readily reacted with triethylsilane-boron trifluoride etherate at room temperature to give only the cis- tetrahydropyranol derivatives via C,-O, bond cleavage. Threo-and erythro-alcohols were prepared selectively from the endo- and exo-ketal, respectively. Dehydrated products also formed when the tertiary alcohol was involved under these reaction conditions. However, the cleavage reaction with aluminum hydride gave the trans-tetrahydropyranol as the major product without dehydration.

Results and Discussion EXPERIMENTAL REFERENCES AND NOTES

Stereoselective Synthesis of Cyclic Ether Compounds via Reductive Cleavage of Bicyclic Ketals
Stereoselective Synthesis of Cyclic Ether Compounds via Reductive Cleavage of Bicyclic Ketals

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Stereoselective Synthesis of Cyclic Ether Compounds via Reductive Cleavage of Bicyclic Ketals Stereoselective Synthesis of Cyclic Ether Compounds via Reductive Cleavage of Bicyclic Ketals

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Stereoselective Synthesis of Cyclic Ether Compounds via Reductive Cleavage of Bicyclic Ketals
Stereoselective Synthesis of Cyclic Ether Compounds via Reductive Cleavage of Bicyclic Ketals

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