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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
Authors
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
Further Information
Publication History
Publication Date:
18 January 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.
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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.
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