Reported herein is a method for the efficient syntheses of optically active 1-alkyl homoallylic amines in yields up to 95%, 13.5:1 dr, and 98% ee under mild, aqueous reaction conditions, via the Rh-catalyzed asymmetric allylation of aliphatic aldimines. This method provides a streamlined synthetic platform for the preparation of indolizidine and piperidine alkaloids, thus demonstrating its usefulness.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1021/acs.orglett.0c02069 | DOI Listing |
Org Lett
December 2024
Leibniz Institute for Catalysis e.V., Albert-Einstein-Str. 29a, 18059 Rostock, Germany.
Herein we present photoinduced cobaloxime-catalyzed selective remote desaturation of aliphatic alcohols. This transformation, which proceeds efficiently at room temperature, facilitates the synthesis of valuable cyclic and acyclic allylic and homoallylic alcohols from readily available saturated aliphatic alcohols. Remarkably, this method obviates the need for external oxidants, noble metal catalysts, and phosphine ligands.
View Article and Find Full Text PDFPolymers (Basel)
November 2024
Centro de Investigación en Química Aplicada, Department of Macromolecular Chemistry and Nanomaterials, Blvd Enrique Reyna #140, Saltillo 25294, Mexico.
Three novel bio-based monomers were synthesized through an amidation reaction involving allylated derivatives of coumaric, ferulic and phloretic acid and a diamine obtained from a thiol-ene coupling reaction between limonene and cysteamine. The monomers containing the enone bond of the cinnamic moiety underwent photoisomerization and photocycloaddition reactions upon UV light irradiation. All three monomers were photocured via thiol-ene photopolymerization using a glycerol-derived trifunctional thiol, resulting in fully bio-based poly(amide-thioether)s.
View Article and Find Full Text PDFOrg Biomol Chem
December 2024
Interdisciplinary Research Center for Catalytic Chemistry, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Ibaraki 305-8565, Japan.
A continuous-flow method for the direct oxidation of alcohols to carboxylic acids is reported, employing hydrogen peroxide (HO) and a platinum (Pt) catalyst within a flow reactor system. This approach allows for precise control over the contact time between the reactants and the catalyst, enabling optimization of reaction conditions. By analyzing the yields of both aldehydes and carboxylic acids as a function of weight hourly space velocity (WHSV), selective synthesis of carboxylic acids was achieved without the formation of corresponding aldehydes.
View Article and Find Full Text PDFChemistry
November 2024
Frontiers Science Center for Transformative Molecules, Zhangjiang Institute for Advanced Study, and Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240, China.
The daunting challenges in converting alcoholic O-H bonds with high bond-dissociation energy (BDE) to alkoxy radicals and harnessing those unruly reaction species largely limit exploiting free alcohols in C(sp)-H functionalization. Herein we describe a novel radical alkynylation and allylation of unactivated C(sp)-H bonds with unmodified aliphatic alcohols. The use of phenyliodine bis(trifluoroacetate) (PIFA) enables the formation of alkoxy radicals under mild photochemical conditions.
View Article and Find Full Text PDFJ Org Chem
November 2024
Department of Chemistry, School of Chemistry, Xi'an Key Laboratory of Sustainable Energy Material Chemistry, MOE Key Laboratory for Nonequilibrium Synthesis and Modulation of Condensed Matter, Xi'an Jiao Tong University, Xi'an 710049, P. R. China.
Aliphatic allylic amines are present in a large number of complex and pharmaceutically relevant molecules. The direct amination of allylic electrophiles serves as the most common method toward the preparation of these motifs. However, the use of feedstock reaction components (allyl alcohol and aliphatic amine) in these transformations remains a great challenge.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!