Stereoselective synthesis of cyclic ether compounds via reductive cleavage of bicyclic ketals

✍ Scribed by Jong-Gab Jun

• Publisher: Journal of Heterocyclic Chemistry
• Year: 1997
• Tongue: English
• Weight: 286 KB
• Volume: 34
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570340247

✦ Synopsis

Abstract

Bicyclic ketals in the 6,8‐dioxabicyclo[3.2.1]octane system readily reacted with triethylsilane‐boron tri‐fluoride etherate at room temperature to give only the cis‐tetrahydropyranol derivatives via C~5~‐O~6~ bond cleavage. Three‐ 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.