7459-72-5Relevant articles and documents
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.
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.
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.
