RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000131.xml
PDF herunterladen
Synfacts 2017; 13(02): 0159
DOI: 10.1055/s-0036-1589876
DOI: 10.1055/s-0036-1589876
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
Enantioselective Coupling of Diazoalkanes with Terminal Alkynes
Autor*innen
Chu W.-D, Zhang L, Zhang Z, Zhou Q, Mo F, Zhang Y, Wang J * Peking University, Beijing and State Key Laboratory of Organometallic Chemistry, Shanghai,
P. R. of China
Enantioselective Synthesis of Trisubstituted Allenes via Cu(I)-Catalyzed Coupling of Diazoalkanes with Terminal Alkynes.
J. Am. Chem. Soc. 2016;
138: 14558-14561
Enantioselective Synthesis of Trisubstituted Allenes via Cu(I)-Catalyzed Coupling of Diazoalkanes with Terminal Alkynes.
J. Am. Chem. Soc. 2016;
138: 14558-14561
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
18. Januar 2017 (online)
Significance
An enantioselective coupling reaction of aryldiazoalkanes with terminal alkynes is described. A copper complex promotes this transformation to afford trisubstituted allenes with high enantioselectivities. A rational stereocontrol model is proposed.
Comment
This reaction involves copper(I) carbene formation, alkynyl migratory insertion, and protonation. The authors suggest that migratory insertion of the copper(I) carbene species is the enantiodetermining step.