174460-88-9Relevant academic research and scientific papers
Easy eco-friendly phenonium ion production from phenethyl alcohols in dimethyl carbonate
Barontini,Proietti Silvestri,Nardi,Bovicelli,Pari,Gallucci,Spezia,Righi
supporting information, p. 5004 - 5006 (2013/08/28)
An efficient and simple one-pot procedure for selective etherification of 2-aryl-ethylalcohols has been achieved through Amberlyst 15-catalyzed reaction in dimethyl carbonate (DMC). Moreover, the polymer catalyst could be recovered and reused with no effect on its activity. The reaction mechanism involves the formation of phenonium ion which has been demonstrated by a C-C bond forming reaction. Theoretical studies are in agreement with and thus explain experimental results.
Ether-directed ortho-C-H olefination with a palladium(II)/monoprotected amino acid catalyst
Li, Gang,Leow, Dasheng,Wan, Li,Yu, Jin-Quan
supporting information, p. 1245 - 1247 (2013/03/13)
Weak coordination is powerful! A PdII-catalyzed olefination of ortho-C-H bonds of arenes directed by weakly coordinating ethers is developed by using monoprotected amino acid (MPAA) ligands. This finding provides a method for chemically modifying ethers, which are abundant in natural products and drug molecules. HFIP=hexafluoroisopropanol. Copyright
Synthesis of chiral chromans by the Pd-catalyzed asymmetric allylic alkylation (AAA): Scope, mechanism, and applications
Trost, Barry M.,Shen, Hong C.,Dong, Li,Surivet, Jean-Philippe,Sylvain, Catherine
, p. 11966 - 11983 (2007/10/03)
The Pd-catalyzed asymmetric allylic alkylation (AAA) of phenol allyl carbonates serves as an efficient strategy to construct the allylic C-O bond allowing access to chiral chromans in up to 98% ee. The effect of pH and the influence of olefin geometry, as well as substitution pattern on the ee and the absolute configuration of the chiral chromans were explored in detail. These observations suggest a mechanism involving the cyclization of the more reactive π-allyl palladium diastereomeric intermediate as the enantiodiscriminating step (Curtin-Hammett conditions). This methodology led to the enantioselective synthesis of the vitamin E core, the first enantioselective total synthesis of (+)-clusifoliol and (-)-siccanin, and the synthesis of an advanced intermediate toward (+)-rhododaurichromanic acid A.
