Allyl ethyl carbonate/palladium (0), a new system for the one step conversion of alcohols into allyl ethers under neutral conditions

✍ Scribed by R. Lakhmiri; P. Lhoste; D. Sinou

• Publisher: Elsevier Science
• Year: 1989
• Tongue: French
• Weight: 212 KB
• Volume: 30
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)80770-x

✦ Synopsis

Alcohols are converted in a one-step procedure into ally1 ethers under neutral conditions, using ally1 ethyl carbonate in the presence of a catalytic amount of palladium (0). Anomeric hydroxyls are selectively allylated in the presence of other hydroxyl groups.

Ally1 groups have been found to be of general use as temporary hydroxyl-protecting groups in sugar chemistry l-3. The successful application of the ally1 group in carbohydrate chemistry is mainly due to its relative stability during glycosidation or deblocking procedures which lead to the removal of other protecting groups.

An ally1 ether can be synthesised by treatment of a free hydroxyl group with 3-halopropene in the presence of base 1. Compounds containing base labile groups can be allylated using allyltrichloro-acetamidate