Literature DB >> 18844412

Highly enantio- and diastereoselective mannich reactions of chiral Ni(II) glycinates with amino sulfones. Efficient asymmetric synthesis of aromatic alpha,beta-diamino acids.

Jiang Wang1, Ting Shi, Guanghui Deng, Hualiang Jiang, Hong Liu.   

Abstract

This paper describes a practical, enantio- and diastereoselective Mannich reaction between a chiral Ni(II) complex of glycine 1 and alpha-amino sulfones 2, involving the creation of a carbon-carbon bond and two stereogenic centers in a single operation; it represents an attractive route to the synthesis alpha,beta-diamino acids.

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Year:  2008        PMID: 18844412     DOI: 10.1021/jo8019169

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  3 in total

1.  Hydrolysis of a Ni-Schiff-Base Complex Using Conditions Suitable for Retention of Acid-labile Protecting Groups.

Authors:  Cory A Bontrager; Tanner J Geibel; George A Lengyel
Journal:  J Vis Exp       Date:  2017-04-06       Impact factor: 1.355

2.  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

3.  Synthesis and stereochemical assignments of diastereomeric Ni(II) complexes of glycine Schiff base with (R)-2-(N-{2-[N-alkyl-N-(1-phenylethyl)amino]acetyl}amino)benzophenone; a case of configurationally stable stereogenic nitrogen.

Authors:  Hiroki Moriwaki; Daniel Resch; Hengguang Li; Iwao Ojima; Ryosuke Takeda; José Luis Aceña; Vadim A Soloshonok
Journal:  Beilstein J Org Chem       Date:  2014-02-19       Impact factor: 2.883

  3 in total

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