115580-41-1Relevant articles and documents
General allylic C-H alkylation with tertiary nucleophiles
Howell, Jennifer M.,Liu, Wei,Young, Andrew J.,White, M. Christina
supporting information, p. 5750 - 5754 (2014/05/06)
A general method for intermolecular allylic C-H alkylation of terminal olefins with tertiary nucleophiles has been accomplished employing palladium(II)/bis(sulfoxide) catalysis. Allylic C-H alkylation furnishes products in good yields (avg. 64%) with excellent regio- and stereoselectivity (>20:1 linear:branched, >20:1 E:Z). For the first time, the olefin scope encompasses unactivated aliphatic olefins as well as activated aromatic/heteroaromatic olefins and 1,4-dienes. The ease of appending allyl moieties onto complex scaffolds is leveraged to enable this mild and selective allylic C-H alkylation to rapidly diversify phenolic natural products. The tertiary nucleophile scope is broad and includes latent functionality for further elaboration (e.g., aliphatic alcohols, α,β-unsaturated esters). The opportunities to effect synthetic streamlining with such general C-H reactivity are illustrated in an allylic C-H alkylation/Diels-Alder reaction cascade: a reactive diene is generated via intermolecular allylic C-H alkylation and approximated to a dienophile contained within the tertiary nucleophile to furnish a common tricyclic core found in the class I galbulimima alkaloids.
PALLADIUM CATALYZED C-ALLYLATION OF HIGHLY ACIDIC CARBO AND HETEROCYCLIC β-DICARBONYL COMPOUNDS
Prat, M.,Moreno-Manas, M.,Ribas, J.
, p. 7205 - 7212 (2007/10/02)
Highly acidic carbo and heterocyclic β-dicarbonyl compounds such as barbituric acid, 3,5-dimethyl-2H-1,2,6-thiadiazine 1,1-dioxide, cyclohexane-1,3-dione, tetronic acids, Meldrum acid and 1,2-diphenylpyrazolidine-3,5-dione are efficiently C-allylated with primary and secondary allylating agents under palladium catalysis.
