1240239-19-3Relevant academic research and scientific papers
Enantioselective N-propargylation of indoles via Cu-catalyzed propargylic alkylation/dehydrogenation of indolines
Zhu, Fulin,Hu, Xiangping
, p. 86 - 92 (2015)
The synthesis of optically active N-propargylindoles has been accomplished via the Cu-catalyzed asymmetric propargylic alkylation of indolines with propargylic esters, followed by the dehydrogenation of the resulting N-substituted indolines with 2,3-dichl
A hand natural alkyne propyl amine compound catalytic asymmetric synthesis method
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Paragraph 0044; 0057; 0079-0083, (2018/02/04)
The invention provides a catalytic asymmetric synthesis method of chiral propargyl amine compounds. The catalytic asymmetric synthesis method is characterized by catalyzing asymmetric decarboxylation reactions in molecules of amide propargyl carbonate com
Copper-catalyzed asymmetric propargylic amination of propargylic acetates with amines using BICMAP
Mino, Takashi,Taguchi, Hiroyuki,Hashimoto, Masatoshi,Sakamoto, Masami
, p. 1520 - 1523 (2013/12/04)
The copper-catalyzed asymmetric propargylic amination of propargylic acetates 1 with amines 2 using BICMAP as a chiral ligand gave the desired products 3 in good yields and with moderate to high enantioselectivities (up to 90% ee).
Copper-catalyzed enantioselective propargylic amination of propargylic esters with amines: Copper-allenylidene complexes as key intermediates
Hattori, Gaku,Sakata, Ken,Matsuzawa, Hiroshi,Tanabe, Yoshiaki,Miyake, Yoshihiro,Nishibayashi, Yoshiaki
supporting information; experimental part, p. 10592 - 10608 (2010/09/10)
The scope and limitations of the copper-catalyzed propargylic amination of various propargylic esters with amines are presented, where optically active diphosphines such as Cl-MeO-BIPHEP and BINAP work as good chiral ligands. A variety of secondary amines are available as nucleophiles for this catalytic reaction to give the corresponding propargylic amines with a high enantioselectivity. The results of some stoichiometric and catalytic reactions indicate that the catalytic amination proceeds via copper-allenylidene complexes formed in situ, where the attack of amines to the electrophilic γ-carbon atom in the allenylidene complex is an important step for the stereoselection. Investigation of the relative rate constants for the reaction of several para-substituted propargylic acetates with N-methylanilines reveals that the formation of the copper-allenylidene complexes is involved in the rate-determining step. The result of the density functional theory calculation on a model reaction also supports the proposed reaction pathway involving copper-allenylidene complexes as key intermediates. The catalytic procedure presented here provides a versatile and direct method for the preparation of a variety of chiral propargylic amines.
