25017-79-2Relevant articles and documents
Visible-light-driven palladium-catalyzed Dowd-Beckwith ring expansion/C-C bond formation cascade
Chen, Li,Guo, Li-Na,Liu, Shuai,Liu, Le,Duan, Xin-Hua
, p. 1791 - 1795 (2021/02/22)
A visible-light-induced palladium-catalyzed Dowd-Beckwith ring expansion/C-C bond formation cascade is described. A range of six to nine-membered β-alkenylated cyclic ketones possessing a quaternary carbon center were accessed under mild conditions. Besides styrenes, the electron-rich alkenes such as silyl enol ethers and enamides were also compatible, providing the desired β-alkylated cyclic ketones in moderate to good yields.
Biocatalytic synthesis of chiral cyclic γ-oxoesters by sequential C-H hydroxylation, alcohol oxidation and alkene reduction
Brenna, Elisabetta,Crotti, Michele,Gatti, Francesco G.,Monti, Daniela,Parmeggiani, Fabio,Pugliese, Andrea,Tentori, Francesca
supporting information, p. 5122 - 5130 (2017/11/09)
A three-step biocatalytic procedure is described for the conversion of methyl and ethyl cyclopentene- and cyclohexenecarboxylates into both the enantiomers of the corresponding chiral 3-oxoesters, which are useful building blocks for the synthesis of active pharmaceutical ingredients. The allylic hydroxylation of the starting cycloalkenecarboxylates is carried out by using R. oryzae resting cells entrapped in alginate beads, in acetate buffer solution at 25 °C. The oxidation of the intermediate allylic alcohols to unsaturated ketones, performed by the laccase/TEMPO system, and the ene-reductase mediated hydrogenation of the alkene bond were carried out in the same reaction vessel in a sequential mode at 30 °C. Being entirely biocatalytic, our multistep procedure provides considerable advantages in terms of selectivity and environmental impact over reported chemical methods.
Control of the Birch Reduction of m-Anisic Acid to Produce Specific 3-Oxocyclohexenecarboxylic Acids
Webster, Francis X.,Silverstein, Robert M.
, p. 922 - 924 (2007/10/02)
An efficient method is reported of synthesizing relatively large quantities of methyl 3-oxo-1-cyclohexenecarboxylate (2b), a useful dienophile and photoreagent, from m-anisic acid (3) through the Birch reduction.Treating 3 with lithium in liquid ammonia p