124389-38-4Relevant articles and documents
Synthesis of homoallyl ethers via allylation of acetals in ionic liquids catalyzed by trimethylsilyl trifluoromethanesulfonate
Zerth, Herbert M.,Leonard, Nicholas M.,Mohan, Ram S.
, p. 55 - 57 (2003)
(Matrix presented) The chemoselective allylation of acetals using allyltrimethylsilane in ionic liquids is catalyzed by TMS triflate (5.0-20.0 mol %). The reaction proceeds smoothly at room temperature to afford the corresponding homoallyl ether in good y
Hydroxyl-directed stereoselective diboration of alkenes
Blaisdell, Thomas P.,Caya, Thomas C.,Zhang, Liang,Sanz-Marco, Amparo,Morken, James P.
, p. 9264 - 9267 (2014/07/21)
An alkoxide-catalyzed directed diboration of alkenyl alcohols is described. This reaction occurs in a stereoselective fashion and is demonstrated with cyclic and acyclic homoallylic and bishomoallylic alcohol substrates. After oxidation, the reaction generates 1,2-diols such that the process represents a method for the stereoselective directed dihydroxylation of alkenes.
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.
