TY - JOUR
T1 - The first allylation of esters by an allylsilane
T2 - One-pot domino synthesis of triallylmethane derivatives
AU - Bandi, Chenna Kesava Reddy
AU - Belostotskii, Anatoly
AU - Hassner, Alfred
PY - 2014/8/11
Y1 - 2014/8/11
N2 - We report the first successful allylation of aromatic esters by allyltrimethylsilane. The reaction is mediated by 0.3-1.0equiv. of titanium tetrachloride (TiCl4) 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.
AB - We report the first successful allylation of aromatic esters by allyltrimethylsilane. The reaction is mediated by 0.3-1.0equiv. of titanium tetrachloride (TiCl4) 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.
KW - Lewis acids
KW - allylation
KW - allylsilanes
KW - esters
KW - triallylmethanes
UR - http://www.scopus.com/inward/record.url?scp=84906075788&partnerID=8YFLogxK
U2 - 10.1002/adsc.201400296
DO - 10.1002/adsc.201400296
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SN - 1615-4150
VL - 356
SP - 2661
EP - 2670
JO - Advanced Synthesis and Catalysis
JF - Advanced Synthesis and Catalysis
IS - 11-12
ER -