
Regio- and Stereoselective Catalytic Addition of Amides to Alkynes
Mathieu BlanchotThe enamide moiety is an important substructure often encountered in biologically active compounds and synthetic drugs. Furthermore, enamides and their derivatives are versatile synthetic intermediates for polymerization, [4+2] cycloaddition, crosscoupling, Heck-olefinination, Halogenation, enantioselective addition or asymmetric hydrogenation. Traditional syntheses of this important substrate class involve rather harsh reaction conditions such as high temperatures and/or the use of strong bases. Based on previous work on the addition of secondary amides to alkynes, a new broadly applicable protocol for the catalytic addition of N-nucleophiles such as primary amides, imides and thioamides to terminal alkynes was developed. The choice of ligands and additives determines the regiochemical outcome so that with two complementary catalyst systems, both the E-anti-Markovnikov products and the Z-anti-Markovnikov products can be synthesized highly regio- and stereoselectively.
17 Jun 2005 ... However, a regio‐ and stereoselective construction of enamide substructures is not at all trivial. Traditional syntheses—for example, from ...
Technik
PC und Mac
Lesen Sie das eBook direkt nach dem Herunterladen über "Jetzt lesen" im Browser, oder mit der kostenlosen Lesesoftware Adobe Digital Editions.
iOS & Android
Für Tablets und Smartphones: Unsere Gratis tolino Lese-App
Andere eBook Reader
Laden Sie das eBook direkt auf dem Reader im www.kauf-gebrauchtes.de Shop herunter oder übertragen Sie es mit der kostenlosen Software Sony READER FOR PC/Mac oder Adobe Digital Editions.
Reader
Öffnen Sie das eBook nach der automatischen Synchronisation auf dem Reader oder übertragen Sie es manuell auf Ihr tolino Gerät mit der kostenlosen Software Adobe Digital Editions.
Marketplace
Aktuelle Bewertungen

Catalysis Science & Technology The stereoselective anti-addition of selenoboranes to α,β-acetylenic esters and amides was achieved in a transition metal-free context using catalytic amounts of PCy 3. The reaction provides anti-3,4-selenoboration with concomitant delivery of α-vinyl selenides by protodeboronation with MeOH. Interest-

Catalysis Science & Technology The stereoselective anti-addition of selenoboranes to α,β-acetylenic esters and amides was achieved in a transition metal-free context using catalytic amounts of PCy 3. The reaction provides anti-3,4-selenoboration with concomitant delivery of α-vinyl selenides by protodeboronation with MeOH. Interest-

Ru-Catalyzed Anti-Markovnikov Addition of Amides to Alkynes: A Regio- and Stereoselective Synthesis of Enamides. Lukas J. Gooßen*, Jan E. Rauhaus, ... Angew Chem Int Ed Engl. 2005 Jun 27;44(26):4042-5. Ru-catalyzed anti- Markovnikov addition of amides to alkynes: a regio- and stereoselective synthesis of ...

Silver-Catalyzed Regio- and Stereoselective … A regio- and stereoselective silver-catalyzed formal carbene insertion into 1,3-dicarbonyls has been developed, using N-nosylhydrazones as diazo surrogates.Two new C−C bonds are constructed at the carbenic carbon center through the selective cleavage of the C−C(=O) σ-bond of acyclic 1,3-dicarbonyls, enabling the preparation of various synthetically useful polysubstituted γ-diketones, γ

Facile Regio- and Stereoselective … A facile, highly stereo- and regioselective hydrometalation of alkynes generating alkenylmetal complex is disclosed for the first time from a reaction of alkyne, carboxylic acid, and a zerovalent group 10 transition metal complex M(PEt3)4 (M = Ni, Pd, Pt). A mechanistic study showed that the hydrometalation does not proceed via the reaction of alkyne with a hydridometal generated by the