Stereospecific olefin synthesis via boronic esters. Studies related to prostaglandin synthesis
β Scribed by D.A. Evans; R.C. Thomas; J.A. Walker
- Book ID
- 104212864
- Publisher
- Elsevier Science
- Year
- 1976
- Tongue
- French
- Weight
- 202 KB
- Volume
- 17
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
β¦ Synopsis
The utility of organoboranes in stereospecific olefin synthesis is now well recognized. 2 Of particular interest to us for synthetic studies currently in progress has been the boronmediated cross-coupling reactions shown below (Scheme I) which result in the stereospecific Scheme I R.
π SIMILAR VOLUMES
Thlophene-contalnlng prostaglandln endoperoxlde analogs are readily avallable by addltlon of thlenylpalladlum species to blcycllc oleflns and subsequent treatment with alkenyl or alkynyl organometalllcs. Hydrogenation affords blcycllc and trlcycllc prostanolc acid analogs.
Reactionof vinylboronicacidsendesterswithhypervaient phenyliodanes in the presence of BF-j-Et20 undergoes boron-icdsneexchangeat O "C in dichloromethane yielding vinyl(phenyl)iodoniumtetratluoroborates stereoaekctively withMentionof configuration. @ 1997ElsevierScienceLtd.