55106-21-3Relevant academic research and scientific papers
Heck Arylation of α,β-Unsaturated Aldehydes
Nejjar,Pinel,Djakovitch
, p. 612 - 619 (2003)
The Heck arylation of α,β-unsaturated aldehydes is strongly dependent on the catalyst, the solvent and the base. Optimized conditions yielded either selectively cinnamyl derivatives (83%) or double arylation products (88% based on aryl conversion). A new α-arylation of β,β-disubstituted acrolein is also realized.
A Domino Process toward Functionally Dense Quaternary Carbons through Pd-Catalyzed Decarboxylative C(sp3)-C(sp3) Bond Formation
Guo, Wusheng,Kuniyil, Rositha,Gómez, José Enrique,Maseras, Feliu,Kleij, Arjan W.
supporting information, p. 3981 - 3987 (2018/03/29)
An efficient protocol was developed to construct functionally dense quaternary carbons with concomitant formation of a new Csp3-Csp3 bond via Pd-catalyzed decarboxylative transformation of vinyl cyclic carbonates. This redox-neutral catalytic system features stereocontrolled formation of multisubstituted allylic scaffolds with an aldehyde functionality generated in situ, and it typically can be performed at room temperature without any additives. DFT calculations provide a rationale toward the selective formation of these compounds and reveal a complex mechanism that with the help of microkinetic models is able to reproduce the nontrivial dependence of the identity of the product on the nature of the substituents in the substrate.
Stereochemistry of Carbenic 1,2-Vinyl Shifts
Kirmse, Wolfgang,Kopannia, Siegfried
, p. 1178 - 1184 (2007/10/03)
Various 1-phenylbut-3-enylidenes, (Ph)CCR2CH=CHR', were generated thermally and photolytically from tosylhydrazone (diazo) precursors. 1,2-Vinyl shifts, leading to 1,3-dienes, R′CH=CHC(Ph)=CR2, were found to predominate over γ-C-H insertion (R = Me) and to compete with 1,2-H shifts (R = H). Intramolecular addition to the double bond was detected in the case of R = R′ = Me. The resulting bicyclobutane is thermally stable and does not mediate the vinyl shift. Stereospecific migration of 1-propenyl groups (R′ = Me), with retention of configuration, was observed on thermolysis and direct photolysis of appropriate substrates. These data exclude the intervention of a triplet diradical and point to vinyl migration in the singlet manifold. Benzophenone-sensitized generation of the carbenes led to partial stereomutation but did not provide conclusive evidence for a triplet rearrangement (isomerization of the diene products could not be avoided under these conditions).
Enynones in organic synthesis. 7. Substituent effects on the α-tocopherol-catalyzed cyclization of enynones to methylenecyclopentenones. Convenient syntheses of members of the methylenomycin class of antibiotics
Jacobi,Brielmann,Cann
, p. 5305 - 5316 (2007/10/02)
Substituent effects on the α-tocopherol (vitamin E, 3b) catalyzed cyclization of a wide variety of enynones 1a-z to methylenecyclopentenones 7a-z have been examined, with particular emphasis given to electron-withdrawing and -donating groups at positions
