A New Intramolecular Reaction for the Regioselective Debenzylation or Protection of Alcohols

✍ Scribed by Jacob Madsen; Mikael Bols

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 74 KB
• Volume: 37
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/(sici)1521-3773(19981204)37:22<3177::aid-anie3177>3.0.co;2-a

✦ Synopsis

Strained benzylidene acetals such as 1 can be prepared with a new intramolecular reaction that allows the selective removal of benzyl protecting groups neighboring free OH groups, without attacking other benzyl groups. The mechanism of this reaction, which is useful for carbohydrate synthesis, probably proceeds via ionic intermediates with neighboring group participation.