A new strategy for the Lewis acid-catalyzed cyclopropanation of allylic alcohols.

1995 ◽  
Vol 117 (45) ◽  
pp. 11367-11368 ◽  
Author(s):  
Andre B. Charette ◽  
Christian Brochu
Keyword(s):  
Lewis Acid ◽  
Allylic Alcohols ◽  
New Strategy ◽  
Acid Catalyzed

scholarly journals Synthesis of spiroannulated and 3-arylated 1,2,4-trioxanes from mesitylol and methyl 4-hydroxytiglate by photooxygenation and peroxyacetalization

2010 ◽  
Vol 6 ◽  
Author(s):  
Axel G Griesbeck ◽  
Lars-Oliver Höinck ◽  
Jörg M Neudörfl
Keyword(s):  
Singlet Oxygen ◽  
Lewis Acid ◽  
Allylic Alcohols ◽  
Ene Reaction ◽  
X Ray ◽  
X Ray Crystallography ◽  
Homoallylic Alcohols ◽  
Acid Catalyzed ◽  
Benzaldehyde Derivatives

Cycloalkanones were utilized in the Lewis acid catalyzed peroxyacetalization of ß-hydroperoxy homoallylic alcohols (prepared by the ene reaction of the allylic alcohols mesitylol and methyl 4-hydroxytiglate, respectively, with singlet oxygen) to give spiroannulated 1,2,4-trioxanes 5a–5e and 9a–9e, respectively. A second series of 3-arylated trioxanes 10a–10h, that are available from the hydroperoxy alcohol 4 and benzaldehyde derivatives, was investigated by X-ray crystallography.

Catalytic Carbonyl-Olefin Metathesis of Aliphatic Ketones: Iron(III) HomoDimers as Lewis Acidic Superelectrophiles

2018 ◽  
Author(s):  
Haley Albright ◽  
Paul S. Riehl ◽  
Christopher C. McAtee ◽  
Jolene P. Reid ◽  
Jacob R. Ludwig ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Olefin Metathesis ◽  
Acid Activation ◽  
Lewis Acid Catalysts ◽  
Distinct Mode ◽  
Aliphatic Ketones ◽  
Carbon Carbon Bond ◽  
Metathesis Reactions ◽  
Acid Catalyzed

<div>Catalytic carbonyl-olefin metathesis reactions have recently been developed as a powerful tool for carbon-carbon bond</div><div>formation. However, currently available synthetic protocols rely exclusively on aryl ketone substrates while the corresponding aliphatic analogs remain elusive. We herein report the development of Lewis acid-catalyzed carbonyl-olefin ring-closing metathesis reactions for aliphatic ketones. Mechanistic investigations are consistent with a distinct mode of activation relying on the in situ formation of a homobimetallic singly-bridged iron(III)-dimer as the active catalytic species. These “superelectrophiles” function as more powerful Lewis acid catalysts that form upon association of individual iron(III)-monomers. While this mode of Lewis acid activation has previously been postulated to exist, it has not yet been applied in a catalytic setting. The insights presented are expected to enable further advancement in Lewis acid catalysis by building upon the activation principle of “superelectrophiles” and broaden the current scope of catalytic carbonyl-olefin metathesis reactions.</div>

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