54518-11-5Relevant articles and documents
Synergistic Relay Reactions To Achieve Redox-Neutral α-Alkylations of Olefinic Alcohols with Ruthenium(II) Catalysis
Kan, Jian,Li, Chao-Jun,Li, Chen-Chen,Li, Jianbin,Lv, Leiyang,Qiu, Zihang
supporting information, p. 4544 - 4549 (2020/02/04)
Herein, we report a ruthenium-catalyzed redox-neutral α-alkylation of unsaturated alcohols based on a synergistic relay process involving olefin isomerization (chain walking) and umpolung hydrazone addition, which takes advantage of the interaction between the two rather inefficient individual reaction steps to enable an efficient overall process. This transformation shows the compatibility of hydrazone-type “carbanions” and active protons in a one-pot reaction, and at the same time achieves the first Grignard-type nucleophilic addition using olefinic alcohols as latent carbonyl groups, providing a higher yield of the corresponding secondary alcohol than the classical hydrazone addition to aldehydes does. A broad scope of unsaturated alcohols and hydrazones, including some complex structures, can be successfully employed in this reaction, which shows the versatility of this approach and its suitability as an alternative, efficient means for the generation of secondary and tertiary alcohols.
Catalytic C-H activation of phenylethylamines or benzylamines and their annulation with allenes
Rodrguez, Aleix,Albert, Joan,Ariza, Xavier,Garcia, Jordi,Granell, Jaume,Farrs, Jaume,La Mela, Andrea,Nicols, Ernesto
, p. 9578 - 9585 (2015/02/19)
Tetrahydro-3-benzazepines and tetrahydroisoquinolines are synthesized in one step from allenes and phenylethylamines or benzylamines, respectively. Mechanistically, it is assumed that activation of a C-H bond of an aromatic ring with Pd(II) occurs, directed by the primary amine, leading to the formation of a palladacycle into which an allene then undergoes insertion. The resulting π-allyl intermediate cyclizes to the products by an intramolecular allylic alkylation. The process is particularly useful with 2,3-butadienoates and amines having a quaternary carbon at the α-position. (Chemical Equation Presented).
Biocatalysed synthesis of the enantiomers of the floral odorant Florhydral
Abate, Agnese,Brenna, Elisabetta,Dei Negri, Claudia,Fuganti, Claudio,Serra, Stefano
, p. 899 - 904 (2007/10/03)
The two enantiomers of the floral odorant Florhydral were prepared by enzymatic methods, and their olfactory properties were evaluated. (+)-Florhydral was found to be much more powerful than the (-)-enantiomer.