Literature DB >> 14624558

Asymmetric, catalytic synthesis of alpha-chiral amines using a novel bis(phosphine) monoxide chiral ligand.

Alessandro A Boezio1, Julien Pytkowicz, Alexandre Côté, André B Charette.   

Abstract

We have shown that Me-DuPHOS monoxide (BozPHOS) is a very effective ligand in the copper-catalyzed addition of dialkylzinc to N-phosphinoylimines providing access to alpha-chiral amines. The new ligand is particularly effective for the addition of the lesser reactive dimethylzinc. The major advantages of this process are high yields, broad substrate scope, and high enantioselectivities with low catalyst loading (3 mol %).

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Year:  2003        PMID: 14624558     DOI: 10.1021/ja038291+

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  9 in total

1.  Formation of C-C Bonds via Iridium-Catalyzed Hydrogenation and Transfer Hydrogenation.

Authors:  John F Bower; Michael J Krische
Journal:  Top Organomet Chem       Date:  2011-01-01       Impact factor: 1.311

2.  Asymmetric intramolecular arylcyanation of unactivated olefins via C-CN bond activation.

Authors:  Mary P Watson; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2008-08-30       Impact factor: 15.419

3.  Editing the stereochemical elements in an iridium catalyst for enantioselective allylic amination.

Authors:  Andreas Leitner; Chutian Shu; John F Hartwig
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-05       Impact factor: 11.205

4.  Catalytic asymmetric addition of diorganozinc reagents to N-phosphinoylalkylimines.

Authors:  Alexandre Côté; Alessandro A Boezio; André B Charette
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-02       Impact factor: 11.205

5.  Asymmetric synthesis of nonracemic primary amines via spiroborate-catalyzed reduction of pure (E)- and (Z)-O-benzyloximes: applications toward the synthesis of calcimimetic agents.

Authors:  Wenhua Ou; Sandraliz Espinosa; Héctor J Meléndez; Silvia M Farré; Jaime L Alvarez; Valerie Torres; Ileanne Martínez; Kiara M Santiago; Margarita Ortiz-Marciales
Journal:  J Org Chem       Date:  2013-05-13       Impact factor: 4.354

6.  A rational pre-catalyst design for bis-phosphine mono-oxide palladium catalyzed reactions.

Authors:  Yining Ji; Hongming Li; Alan M Hyde; Qinghao Chen; Kevin M Belyk; Katrina W Lexa; Jingjun Yin; Edward C Sherer; R Thomas Williamson; Andrew Brunskill; Sumei Ren; Louis-Charles Campeau; Ian W Davies; Rebecca T Ruck
Journal:  Chem Sci       Date:  2017-01-19       Impact factor: 9.825

7.  Nitroxyl Surprise: A Simple Amine Additive Revealed as Copper's Co-Catalyst in the Aerobic Oxidation of Alcohols.

Authors:  Mikhail O Konev; Elizabeth R Jarvo
Journal:  ACS Cent Sci       Date:  2017-04-18       Impact factor: 14.553

8.  Manganese(i)-catalyzed access to 1,2-bisphosphine ligands.

Authors:  Luo Ge; Syuzanna R Harutyunyan
Journal:  Chem Sci       Date:  2022-01-13       Impact factor: 9.825

9.  Direct Asymmetric Reductive Amination for the Synthesis of (S)-Rivastigmine.

Authors:  Guorui Gao; Shaozhi Du; Yang Yang; Xue Lei; Haizhou Huang; Mingxin Chang
Journal:  Molecules       Date:  2018-08-31       Impact factor: 4.411

  9 in total

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