Issue 5, 2010
From the journal:

Organic & Biomolecular Chemistry

Chiral N-phosphonyl imine chemistry: an efficient asymmetric synthesis of chiral N-phosphonyl propargylamines†

Parminder Kaur,a   Gaurav Shakya,a   Hao Sun,b   Yi Pan*b  and  Guigen Li*a  

* Corresponding authors

a Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas, USA
E-mail: guigen.li@ttu.edu
Fax: +1-806-742-3015

b School of Chemistry and Chemical Engineering, and the State Key Lab of Coordination Chemistry, Nanjing University, Nanjing, PR China
E-mail: yipan@nju.edu.cn
Fax: +86-25-83314502

Abstract

A variety of substituted chiral propargylamines have been synthesized by reacting chiral N-phosphonylimines with lithium aryl/alkyl acetylides. Seventeen examples were studied to give excellent yields (>90%) and diastereoselectivities (96 : 4 to 99 : 1). It was found that the types of bases for generating acetylides and solvents are crucial for effectiveness of this asymmetric reaction. In addition, N,N-isopropyl group on chiral N-phosphonylimine auxiliary was proven to be superior to other protecting groups in controlling diastereoselectivity.

Graphical abstract: Chiral N-phosphonyl imine chemistry: an efficient asymmetric synthesis of chiral N-phosphonyl propargylamines

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Article information

DOI
https://doi.org/10.1039/B923914F
Article type
Paper
Submitted
13 Nov 2009
Accepted
25 Nov 2009
First published
05 Jan 2010

Org. Biomol. Chem., 2010,8, 1091-1096

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Chiral N-phosphonyl imine chemistry: an efficient asymmetric synthesis of chiral N-phosphonyl propargylamines

P. Kaur, G. Shakya, H. Sun, Y. Pan and G. Li, Org. Biomol. Chem., 2010, 8, 1091 DOI: 10.1039/B923914F

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