Stereoselective synthesis of either E- or Z-diiodoalkenes from alkynes using ICI and iodide
✍ Scribed by Nadine Hénaff; Sarah K Stewart; Andrew Whiting
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 127 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
Reaction of alkynes with ICI and an iodide source results in the stereoselective formation of diiodoalkenes in moderate to high yield. At r.t., the reaction is stereospecific, resulting in the formation of E-diiodoalkenes, however lowering the temperature mad using a more soluble iodide som'ee results in a stereoselective formation of the Z-diiodoalkenes.
📜 SIMILAR VOLUMES
The )'-(t~-hydroxylalkyl)butenolides lk-5 and ul-5 were prepared by Mukaiyama aldol additions between iodoaldehyde 10 and the trimethylsiloxy-substituted furan 6 in the presence of BF3eOEt2 and ZnBr2, respectively. Couplings of these butenolides with 3-ethynylfuran followed by anti-eliminations
Alkylidenebutenolides from a 2-(Trimethylsiloxy)furan and Iodomethacrolein -Stereoselective Synthesis of Z-and E-Freelingyne. -Via an aldol/β-elimination approach as key sequence the title products such as (V) and (VI) are prepared. It is noteworthy that an earlier described method with triflic anh
## 3-(Diphenylphosphinojalfylltftanium reagent qenerated easily from allyldiphenylphosphine condenses with aldehydes to give (Z)-1,3-alkadienes in a highly reqio-and stereoselective manner. In contrast, lithiated allyldiphenylphosphine oxide condenses with aldehydes to give (El-1,3-alkadienes dir