Premium
The First Allylation of Esters by an Allylsilane: One‐Pot Domino Synthesis of Triallylmethane Derivatives
Author(s) -
Bandi Chenna Kesava Reddy,
Belostotskii Anatoly,
Hassner Alfred
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400296
Subject(s) - chemistry , titanium tetrachloride , steric effects , domino , phenol , nucleophile , denticity , titanium , ring (chemistry) , cascade reaction , organic chemistry , medicinal chemistry , catalysis , crystal structure
We report the first successful allylation of aromatic esters by allyltrimethylsilane. The reaction is mediated by 0.3–1.0 equiv. of titanium tetrachloride (TiCl 4 ) at room temperature and leads in a multi‐step, one‐pot reaction to quaternary triallylmethane derivatives 5 . The most efficient ester possessed two ortho ‐methoxy substituents on the phenol ring. Molecular modelling revealed the ability of this compound to form a bidentate titanium complex, thus improving the steric accessibility of the ester carbonyl to nucleophilic attack.