1228296-10-3Relevant articles and documents
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.