7459-72-5Relevant academic research and scientific papers
Enantioselective template-directed [2+2] photocycloadditions of isoquinolones: Scope, mechanism and synthetic applications
Coote, Susannah C.,P?thig, Alexander,Bach, Thorsten
supporting information, p. 6906 - 6912 (2015/04/27)
A strategy for the enantioselective [2+2] photocycloaddition of isoquinolones with alkenes is presented, in which the formation of a supramolecular complex between a chiral template and the substrate ensures high enantioface differentiation by shielding one face of the substrate. Fifteen different electron-deficient alkenes and ten different substituted isoquinolones undergo efficient photocycloaddition, yielding the cyclobutane products in excellent yields and with outstanding regio-, diastereo- and enantioselectivities (up to 990 ee). The mechanism of the reaction is investigated by means of triplet sensitization/quenching and radical clock experiments, the results of which are consistent with the involvement of a triplet excited state and a 1,4-biradical intermediate. The variety of functionalized cyclobutanes obtained using this approach can be further increased by straightforward synthetic transformations of the photoadducts, allowing rapid access to libraries of compounds for various applications.
Methods and compositions for treating amyloid-related diseases
-
Page/Page column 172-173, (2010/11/24)
Methods, compounds, pharmaceutical compositions and kits are described for treating or preventing amyloid-related disease.
Reactivity of unsaturated sultones synthesized from unsaturated alcohols by ring-closing metathesis. Application to the racemic synthesis of the originally proposed structure of mycothiazole
Le Flohic, Alexandre,Meyer, Christophe,Cossy, Janine
, p. 9017 - 9037 (2007/10/03)
Unsaturated sultones have been synthesized from various primary or secondary alkenols by ring-closing metathesis of the corresponding unsaturated sulfonates. By treatment with a strong base, β,γ-unsaturated sultones can be metalated and subsequently alkylated with electrophiles. When iodomethylmagnesium chloride was selected as the electrophile, seven-membered ring β,γ-unsaturated sultones were converted into homoallylic conjugated (Z)-dienols. This methodology was applied to the racemic synthesis of the originally proposed structure of the marine natural product mycothiazole.
Ring closing metathesis in the synthesis of sultones and sultams
Karsch, Sandra,Freitag, Dirk,Schwab, Pia,Metz, Peter
, p. 1696 - 1712 (2007/10/03)
Unsaturated sultones with normal, medium and large ring sizes were efficiently synthesized by ring closing metathesis (RCM) of sulfonates. The resulting α,β-unsaturated sultones act as dienophiles in intermolecular Diels-Alder reactions. A first cyclic sulfate formation through RCM has been discovered, and a rapid access to β-lactams fused to a sultam moiety of variable ring size was developed from inexpensive, commercially available starting materials using RCM as the key operation. An efficient RCM of 4-vinyl-azetidin-2-ones to give 1-aza-bicyclo[4.2.0]oct-4-en-8-ones is also described.
Unsaturated Sultones from Unsaturated Sulfonates: Synthesis by Ring-Closing Metathesis and Reactivity
Flohic, Alexandre Le,Meyer, Christophe,Cossy, Janine,Desmurs, Jean-Roger,Galland, Jean-Christophe
, p. 667 - 670 (2007/10/03)
Unsaturated sultones can be efficiently synthesized by ring-closing metathesis of the corresponding unsaturated sulfonates derived from primary and secondary alkenols or alkynols. These compounds can be converted to 1,3-dienes under basic conditions in the presence of carbenoid species.
Synthesis of sultones by ring closing metathesis
Karsch, Sandra,Schwab, Pia,Metz, Peter
, p. 2019 - 2022 (2007/10/03)
Unsaturated sultones with normal, medium and large ring sizes were efficiently synthesized by ring closing metathesis of sulfonates. The required substrates were readily derived from alkenols and olefinic sulfonyl chlorides.
