Literature DB >> 19480447

Highly stereoselective metal-free catalytic reduction of imines: an easy entry to enantiomerically pure amines and natural and unnatural alpha-amino esters.

Stefania Guizzetti1, Maurizio Benaglia, Sergio Rossi.   

Abstract

A highly efficient catalytic stereoselective ketimine reduction is described. The combination of an inexpensive chiral organocatalyst, easily prepared in a single step, and of a very cheap removable chiral auxiliary allowed us to obtain enantiomerically pure amino compounds. The methodology allowed synthesis of chiral secondary and primary amines and natural and unnatural amino esters in high yields often with total control of the absolute stereochemistry.

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Year:  2009        PMID: 19480447     DOI: 10.1021/ol900945h

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  7 in total

1.  (R)-N,N'-Dimethyl-1,1'-binaphthyldiamine.

Authors:  Scott E Denmark; Pavel G Ryabchuk
Journal:  Organic Synth       Date:  2019-09-27

2.  Synthesis and separation of the enantiomers of the neuropeptide S receptor antagonist (9R/S)-3-oxo-1,1-diphenyl-tetrahydro-oxazolo[3,4-a]pyrazine-7-carboxylic acid 4-fluoro-benzylamide (SHA 68).

Authors:  Claudio Trapella; Michela Pela; Luisa Del Zoppo; Girolamo Calo; Valeria Camarda; Chiara Ruzza; Alberto Cavazzini; Valentina Costa; Valerio Bertolasi; Rainer K Reinscheid; Severo Salvadori; Remo Guerrini
Journal:  J Med Chem       Date:  2011-04-05       Impact factor: 7.446

3.  Highly efficient diastereoselective reduction of alpha-fluoroimines.

Authors:  Roy M Malamakal; Whitney R Hess; Todd A Davis
Journal:  Org Lett       Date:  2010-05-21       Impact factor: 6.005

4.  Design and synthesis of 3,3'-triazolyl biisoquinoline N,N'-dioxides via Hiyama cross-coupling of 4-trimethylsilyl-1,2,3-triazoles.

Authors:  Shiyu Sun; Carlyn Reep; Chenrui Zhang; Burjor Captain; Roberto Peverati; Norito Takenaka
Journal:  Tetrahedron Lett       Date:  2021-08-21       Impact factor: 2.032

5.  A one pot protocol to convert nitro-arenes into N-aryl amides.

Authors:  Elisabetta Massolo; Margherita Pirola; Alessandra Puglisi; Sergio Rossi; Maurizio Benaglia
Journal:  RSC Adv       Date:  2020-01-23       Impact factor: 4.036

6.  Enantioselective reduction of ketoimines promoted by easily available (S)-proline derivatives.

Authors:  Martina Bonsignore; Maurizio Benaglia; Laura Raimondi; Manuel Orlandi; Giuseppe Celentano
Journal:  Beilstein J Org Chem       Date:  2013-04-02       Impact factor: 2.883

7.  Synthesis of chiral N-phosphinyl α-imino esters and their application in asymmetric synthesis of α-amino esters by reduction.

Authors:  Yiwen Xiong; Haibo Mei; Lingmin Wu; Jianlin Han; Yi Pan; Guigen Li
Journal:  Beilstein J Org Chem       Date:  2014-03-13       Impact factor: 2.883

  7 in total

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