52149-13-0Relevant 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.
TRIMETHYLSILYL TRIFLATE CATALYZED ALDOL-TYPE REACTION OF ENOL SILYL ETHERS AND ACETALS OR RELATED COMPOUNDS
Murata, Shizuaki,Suzuki, Chikusa,Noyori, Ryoji
, p. 4259 - 4276 (2007/10/02)
Trimethylsilyl triflate with or without added hindered tertiary amines catalyzes directed condensation of enol trimethylsilyl ethers with acetals, orthoformate, or 2-acetoxytetrahydrofuran or -pyrans to give the corresponding β-alkoxy carbonyl compounds.R
DIASTEREOSELECTIVE REACTION OF CROTYLSILANES WITH ACETALS. IMPORTANCE OF THE ELECTRONIC EFFECT IN ACYCLIC STEREOSELECTION
Hosomi, Akira,Ando, Masatomo,Sakurai, Hideki
, p. 365 - 368 (2007/10/02)
Acyclic stereoselection of aromatic acetals in the reaction with crotylsilanes depends upon the geometry of crotylsilanes.It was also disclosed for the first time that the electronic effect plays an important role on controlling the diastereochemistry.