868944-54-1Relevant academic research and scientific papers
Iron-Catalyzed Anti-Markovnikov Hydroamination and Hydroamidation of Allylic Alcohols
Ma, Wei,Zhang, Xiaohui,Fan, Juan,Liu, Yuxuan,Tang, Weijun,Xue, Dong,Li, Chaoqun,Xiao, Jianliang,Wang, Chao
supporting information, p. 13506 - 13515 (2019/09/09)
Hydroamination allows for the direct access to synthetically important amines. Controlling the selectivity of the reaction with efficient, widely applicable, and economic catalysts remains challenging, however. This paper reports an iron-catalyzed formal anti-Markovnikov hydroamination and hydroamidation of allylic alcohols, which yields γ-amino and γ-amido alcohols, respectively. Homoallylic alcohol is also feasible. The catalytic system, consisting of a pincer Fe-PNP complex (1-4 mol %), a weak base, and a nonpolar solvent, features exclusive anti-Markovnikov selectivity, broad substrate scope (>70 examples), and good functional group tolerance. The reaction could be performed at gram scale and applied to the synthesis of drug molecules and heterocyclic compounds. When chiral substrates are used, the stereochemistry and enantiomeric excess are retained. Further application of the chemistry is seen in the functionalization of amino acids, natural products, and existing drugs. Mechanistic studies suggest that the reaction proceeds via two cooperating catalytic cycles, with the iron complex catalyzing a dehydrogenation/hydrogenation process while the amine substrate acts as an organocatalyst for the Michael addition step.
HYDROXYALKYL DERIVATIVES OF BIOLOGICALLY ACTIVE COMPOUNDS
-
Page/Page column 15-16, (2010/02/14)
Hydroxyalkyl derivatives of biologically active compounds represented by the formula VII wherein R2 = H, CI-12 alkyl, C6-12 aryl, or -OH and D = Biologically active agent having functional groups such as Formula (a) epoxy or aziridine and Z' = Formula (b) L= spacer comprising (un)substituted alkyl, hydroxyalkyl or alkoxy alkyl with the condition that the carbon chain length contains 2 to 6 carbon atoms when Z' = Formula (c) and pharmaceutically acceptable acid addition salts and enantiomers thereof Also process for the synthesis of compounds of the Formula VII and pharmaceutically acceptable acid addition salts and enantiomers thereof comprising condensation of the biologically active agents having functional groups such as Formula (d) epoxy or azifidine with substituted alkyl derivatives under alkaline conditions, at 20 - 80°C, in an organic solvent.
