The directed dihydroxylation of allylic alcohols

✍ Scribed by Timothy J. Donohoe; Peter R. Moore; Michael J. Waring; Nicholas J. Newcombe

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 254 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)01061-7

✦ Synopsis

The preparation and dihydroxylation of a series of polyenes and cyclic ailylic alcohols using the TMEDA/osmium tetroxide mixture is reported. Remarkably, these reagents lead to high levels of regiochemical and stereochemical control as the oxidant hydrogen-bonds to the allylic alcohol group. A mechanistic hypothesis is presented which invokes the formation of a reactive, bidentate complex between osmium tetroxide and TMEDA at low temperatures.