Cp2TiCl2-catalyzed cis-hydroalumination of propargylic amines with Red-Al: stereoselective synthesis of Z-configured allylic amines

Renhong Sun; Jun Liu; Shuang Yang; Ming Chen; Ning Sun; Haoyi Chen; Xin Xie; Xu You; Shi Li; Yuanhong Liu

doi:10.1039/c5cc00950b

Cp2TiCl2-catalyzed cis-hydroalumination of propargylic amines with Red-Al: stereoselective synthesis of Z-configured allylic amines

Chem Commun (Camb). 2015 Apr 14;51(29):6426-9. doi: 10.1039/c5cc00950b.

Authors

Renhong Sun¹, Jun Liu, Shuang Yang, Ming Chen, Ning Sun, Haoyi Chen, Xin Xie, Xu You, Shi Li, Yuanhong Liu

Affiliation

¹ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. China. yhliu@sioc.ac.cn.

PMID: 25765939
DOI: 10.1039/c5cc00950b

Abstract

A titanium-catalyzed cis-hydroalumination of propargylic amines with Red-Al is described, which provides an efficient way to produce Z-configured allylic amines in good to excellent yields with high stereoselectivity and good regioselectivity. The hydride-bridged Al/Ti bimetallic species may act as a real catalyst in this reaction.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Chemistry Techniques, Synthetic
Models, Molecular
Molecular Conformation
Organometallic Compounds / chemistry*
Pargyline / analogs & derivatives*
Pargyline / chemical synthesis
Pargyline / chemistry
Propylamines / chemical synthesis*
Propylamines / chemistry*
Stereoisomerism

Substances

Organometallic Compounds
Propylamines
dihydrobis(2-methoxyethoxy)aluminate
propargylamine
Pargyline
titanocene dichloride