The First Allylation of Esters by an Allylsilane: One‐Pot Domino Synthesis of Triallylmethane Derivatives. Issue 11 (24th June 2014)

• Record Type: Journal Article
• Authors: Bandi, Chenna Kesava Reddy; Belostotskii, Anatoly; Hassner, Alfred
• Is Part Of: Advanced synthesis & catalysis. Volume 356:Issue 11/12(2014)
• Page Start: 2661
• Page End: 2670
• Publication Date: 2014-06-24
• Subjects: Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201400296
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>We report the first successful allylation of aromatic esters by allyltrimethylsilane. The reaction is mediated by 0.3–1.0 equiv. of titanium tetrachloride (TiCl₄) at room temperature and leads in a multi‐step, one‐pot reaction to quaternary triallylmethane derivatives <bold>5</bold>. The most efficient ester possessed two <italic>ortho</italic>‐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.</p> <p> <boxed-text content-type="graphic" position="anchor" orientation="portrait"> <graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgh11pkdqn2" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /> </boxed-text> </p> </abstract>