Literature DB >> 20165799

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

Parminder Kaur1, Gaurav Shakya, Hao Sun, Yi Pan, Guigen Li.   

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.

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Year:  2010        PMID： 20165799     DOI： 10.1039/b923914f

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  12 in total

1.  REGIOSELECTIVE MULTICOMPONENT DOMINO REACTIONS PROVIDING RAPID AND EFFICIENT ROUTES TO FUSED ACRIDINES.

Authors:  Jin-Peng Zhang; Wei Fan; Jie Ding; Bo Jiang; Shu-Jiang Tu; Guigen Li
Journal:  Heterocycles       Date:  2013-12-17       Impact factor: 0.831

2.  An efficient one-pot synthesis of functionalized chromeno[4,3-b]pyridine derivatives under catalyst-free conditions.

Authors:  Yong-Xiang Zheng; Zhan Xun; Juan-Juan Zhang; Zhi-Bin Huang; Da-Qing Shi
Journal:  Mol Divers       Date:  2017-01-31       Impact factor: 2.943

3.  Asymmetric catalytic N-phosphonyl imine chemistry: the use of primary free amino acids and Et2AlCN for asymmetric catalytic Strecker reaction.

Authors:  Parminder Kaur; Suresh Pindi; Walter Wever; Trideep Rajale; Guigen Li
Journal:  J Org Chem       Date:  2010-08-06       Impact factor: 4.354

4.  Asymmetric hydrophosphylation of chiral N-phosphonyl imines provides an efficient approach to chiral α-amino phosphonates.

Authors:  Parminder Kaur; Walter Wever; Trideep Rajale; Guigen Li
Journal:  Chem Biol Drug Des       Date:  2010-10       Impact factor: 2.817

5.  Asymmetric synthesis of α-amino-1,3-dithianes via chiral N-phosphonyl imine-based Umpolung reaction without using chromatography and recrystallization.

Authors:  Padmanabha V Kattamuri; Teng Ai; Suresh Pindi; Yinwei Sun; Peng Gu; Min Shi; Guigen Li
Journal:  J Org Chem       Date:  2011-03-15       Impact factor: 4.354

6.  Design, synthesis, and applications of chiral N-2-phenyl-2-propyl sulfinyl imines for group-assisted purification (GAP) asymmetric synthesis.

Authors:  Suresh Pindi; Jianbin Wu; Guigen Li
Journal:  J Org Chem       Date:  2013-03-26       Impact factor: 4.354

7.  Asymmetric catalytic aza-Morita-Baylis-Hillman reaction for the synthesis of 3-substituted-3-aminooxindoles with chiral quaternary carbon centers.

Authors:  Fang-Le Hu; Yin Wei; Min Shi; Suresh Pindi; Guigen Li
Journal:  Org Biomol Chem       Date:  2013-02-13       Impact factor: 3.876

8.  N,N-DIIsopropyl-N-phosphonyl imines lead to efficient asymmetric synthesis of aziridine-2-carboxylic esters.

Authors:  Padmanabha V Kattamuri; Yiwen Xiong; Yi Pan; Guigen Li
Journal:  Org Biomol Chem       Date:  2013-05-28       Impact factor: 3.876

9.  Asymmetric C-C Bond Formation between Chiral N-Phosphonyl Imines and Ni(II)-Complex of Glycine Schiff Base Provides a GAP Synthesis of α,β-syn-Diamino Acid Derivatives.

Authors:  Hao Sun; Haowei Zhang; Jianlin Han; Yi Pan; Guigen Li
Journal:  European J Org Chem       Date:  2013-08-01

10.  In Situ Immobilized Silver Nanoparticles on Rubia tinctorum Extract-Coated Ultrasmall Iron Oxide Nanoparticles: An Efficient Nanocatalyst with Magnetic Recyclability for Synthesis of Propargylamines by A3 Coupling Reaction.

Authors:  Hojat Veisi; Lida Mohammadi; Saba Hemmati; Taiebeh Tamoradi; Pourya Mohammadi
Journal:  ACS Omega       Date:  2019-08-15
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