135312-64-0Relevant academic research and scientific papers
Unusual carbon-carbon bond formations between allylboronates and acetals or ketals catalyzed by a peculiar indium(I) lewis acid
Schneider, Uwe,Dao, Hai T.,Kobayashi, Shu
supporting information; experimental part, p. 2488 - 2491 (2010/07/05)
InIOTf has been uncovered as an effective Lewis acid catalyst for unprecedented nucleophilic substitution of acetals or ketals with allylboronates. A transmetalative SN1 mechanism is proposed in which a single InI center acts as a dual catalyst to activate both reagents sequentially. Contrary to the classic γ-selectivity of allylsilanes (Hosomi-Sakurai reaction), this InI-catalyzed borono variant displays distinct α-selectivity. Substrate scope and functional group tolerance proved to be excellent.
A Versatile Synthesis of 1,4-Dienes: Use of Vinyl Ethers as Vinyl Cation Equivalents
Ohm, Stefan,Baeuml, Englbert,Mayr, Herbert
, p. 2785 - 2790 (2007/10/02)
The α,β-dibromo ethers 2, in situ generated from the vinyl ethers 1 and bromine, react with the allylsilanes 3 in the presence of ZnCl2 to give the β-bromo ethers 4.Treatment of 4 with Na in diethyl ether yields 1,4-dienes 5 in 62-79percent overall yield.Key Words: Enol ether / Allylsilane / Bromo ether / 1,4-Diene / Alkoxyalkylation
