OsO4-Catalyzed oxidative cyclization of geranyl and neryl acetate to cis-2,5-bis(hydroxymethyl)tetrahydrofurans

✍ Scribed by Marcella de Champdoré; Maria Lasalvia; Vincenzo Piccialli

• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 312 KB
• Volume: 39
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)02172-8

✦ Synopsis

OsO4 catalyzes the oxidative cyclization of the 1,5-dienes geranyl acetate (1) and neryl acetate (2) to the cis-2,5-bis(hydroxymethyl)tetrahydrofurans 3 and 4 respectively, in the presence of NalO4 as cooxidant in DMF. The reaction is stereospecific and proceeds with the sequential syn addition to both double bonds of the starting materials. The observed stereoselectivity can be explained by invoking the intermediacy of a squarebased pyramidal osmium (VI) diester ( 5) that has been isolated and characterized. Evidence is reported that this substance is indeed an intermediate in the transformation of 1 to 3.