127700-63-4Relevant academic research and scientific papers
Overcoming the Deallylation Problem: Palladium(II)-Catalyzed Chemo-, Regio-, and Stereoselective Allylic Oxidation of Aryl Allyl Ether, Amine, and Amino Acids
Begam, Hasina Mamataj,Jana, Ranjan,Manna, Kartic,Samanta, Krishanu
supporting information, p. 7443 - 7449 (2020/10/09)
We report herein a Pd(II)/bis-sulfoxide-catalyzed intramolecular allylic C-H acetoxylation of aryl allyl ether, amine, and amino acids with the retention of a labile allyl moiety. Mechanistically, the reaction proceeds through a distinct double-bond isomerization from the allylic to the vinylic position followed by intramolecular carboxypalladation and the β-hydride elimination pathway. For the first time, C-H oxidation of N-allyl-protected amino acids to furnish five-membered heterocycles through 1,3-syn-addition is established with excellent diastereoselectivity.
Chemoselective Intramolecular Functionalization of Methyl Groups in Nonconstrained Molecules Promoted by N-Iodosulfonamides
Paz, Nieves R.,Rodríguez-Sosa, Dionisio,Valdés, Haydee,Marticorena, Ricardo,Melián, Daniel,Copano, M. Belén,González, Concepción C.,Herrera, Antonio J.
supporting information, p. 2370 - 2373 (2015/06/02)
Mechanistic evidence observed in Hofmann-L?ffler-Freytag-type reactions has been crucial to achieve the chemoselective functionalization of methyl groups under mild conditions. Radical-mediated methyl iodination and subsequent oxidative deiodination are the key steps in this functionalization, where iodine chemistry has a pivotal role on the formation of the C-N bond. The concepts of single hydrogen atom transfer (SHAT) and multiple hydrogen atom transfer (MHAT) are introduced to describe the observed chemoselectivity. (Chemical Equation Presented).
Amino Acid Synthesis via Ring Opening of N-Sulphonyl Aziridine-2-Carboxylate Esters with Organometallic Reagents.
Baldwin, Jack E.,Spivey, Alan C.,Schofield, Christopher J.,Sweeney, Joseph B.
, p. 6309 - 6330 (2007/10/02)
Nucleophilic ring opening of optically active N-sulphonyl aziridine-2-carboxylate esters with organometallic reagents has been investigated as a method of preparation of optically active amino acids.Key Words: aziridine-2-carboxylate, cuprate, nucleophilic ring opening, amino acid
The Ring Opening of Aziridine-2-carboxylate Esters with Organometallic Reagents
Baldwin, Jack E.,Adlington, Robert M.,O'Neil, Ian A.,Schofield, Christopher,Spivey, Alan C.,Sweeney, Joseph B.
, p. 1852 - 1854 (2007/10/02)
The ring opening of aziridines with organocuprate reagents provides a new entry to amino acids.
