Phenylsulfonyl-methylenation of aldonolactones

✍ Scribed by Arnaldo Alzérreca; Eliud Hernández; Edgar Mangual; José A. Prieto

• Book ID: 102341318
• Publisher: Journal of Heterocyclic Chemistry
• Year: 1999
• Tongue: English
• Weight: 348 KB
• Volume: 36
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570360236

✦ Synopsis

Abstract

The low temperature addition of dilithiomethylphenyl sulfone to 2,3‐O‐isopropylidene‐D‐erythronolactone, and to 5‐O‐(tert‐butyldimethylsilyl)‐2,3‐O‐isopropylidene‐D‐ribofuranolactone gives the lactols 2 and 3a, respectively. Dehydration of lactol 2 in the presence of boron trifluoride etherate produces tetrahydrofuranylidene sulfones 5 and 6 in good yields. The reaction of lactol 3a under the same reaction conditions proceeds with formation of the 1′,5′‐anhydro derivative 7 via competing intramolecular substitution.