Literature DB >> 19297153

Chiral N-phosphonyl imine chemistry: asymmetric synthesis of alpha,beta-diamino esters by reacting phosphonyl imines with glycine enolates.

Teng Ai1, Guigen Li.   

Abstract

Chiral phosphonyl imines attached with N-isopropyl protection group were found to react with lithium glycine enolates under convenient conditions to give alpha,beta-diamino esters. Thirteen examples have been examined in good to excellent chemical yields (85-97%) diastereoselectivity (up to 99% de). By treating with HBr at room temperature, the chiral auxiliary can be readily removed and recycled. The absolute structure has been unambiguously determined by converting a product to a known sample.

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Year:  2009        PMID： 19297153     DOI： 10.1016/j.bmcl.2009.03.001

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  8 in total

1.  Microwave-assisted multicomponent reaction in water leading to highly regioselective formation of benzo[f]azulen-1-ones.

Authors:  Shu-Liang Wang; Chuang Cheng; Fei-Yue Wu; Bo Jiang; Feng Shi; Shu-Jiang Tu; Trideep Rajale; Guigen Li
Journal:  Tetrahedron       Date:  2011-06-24       Impact factor: 2.457

2.  GAP Peptide Synthesis via Design of New GAP Protecting Group: An Fmoc/tBu Synthesis of Thymopentin Free from Polymers, Chromatography and Recrystallization.

Authors:  Cole W Seifert; Armando Paniagua; Gabrielle A White; Lucy Cai; Guigen Li
Journal:  European J Org Chem       Date:  2016-03-08

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.  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

7.  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

8.  Asymmetric Carbamoyl Anion Additions to Chiral N-Phosphonyl Imines via the GAP Chemistry Process and Stereoselectivity Enrichments.

Authors:  Cole W Seifert; Suresh Pindi; Guigen Li
Journal:  J Org Chem       Date:  2014-12-09       Impact factor: 4.354
  8 in total

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