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Cu(I)‐Catalyzed Asymmetric Cross‐Coupling of N ‐Tosylhydrazones and Trialkylsilylethynes: Enantioselective Construction of C(sp)—C(sp 3 ) Bonds
Author(s) -
Chu WenDao,
Guo Fangfang,
Yu Lefei,
Hong Junting,
Liu Qianyi,
Mo Fanyang,
Zhang Yan,
Wang Jianbo
Publication year - 2018
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201700633
Subject(s) - chemistry , enantioselective synthesis , phosphoramidite , catalysis , carbene , stereochemistry , coupling (piping) , medicinal chemistry , combinatorial chemistry , organic chemistry , dna , biochemistry , oligonucleotide , mechanical engineering , engineering
The first catalytic enantioselective C(sp)―C(sp 3 ) cross‐coupling reaction between N ‐tosylhydrazones and trialkylsilylethynes in the presence of Cu(I) salts and chiral phosphoramidite ligands was developed. A series of synthetically interesting, functionalized alkynes were obtained with moderate to good enantioselectivities (up to 83% ee). Cu(II) carbene migratory insertion is proposed to be the enantio‐determining step.