Literature DB >> 15176816

Dynamic kinetic resolution of atropisomeric amides.

Vincent Chan1, Jeung Gon Kim, Ciril Jimeno, Patrick J Carroll, Patrick J Walsh.   

Abstract

[reaction: see text] Using L-proline as catalyst in the asymmetric aldol reaction and a series of benzamides and naphthamides, we have accomplished a dynamic kinetic resolution that simultaneously establishes the stereochemistry of the atropisomeric amide's chiral axis and a stereogenic center. The enantioselectivities ranged from 82% to 95% and the diastereoselectivities from 2.1:1 to 7.0:1.

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Year:  2004        PMID: 15176816     DOI: 10.1021/ol0492952

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


  5 in total

1.  Regioselective derivatizations of a tribrominated atropisomeric benzamide scaffold.

Authors:  Kimberly T Barrett; Scott J Miller
Journal:  Org Lett       Date:  2015-01-12       Impact factor: 6.005

2.  Catalytic enantioselective synthesis of atropisomeric biaryls by a cation-directed O-alkylation.

Authors:  John D Jolliffe; Roly J Armstrong; Martin D Smith
Journal:  Nat Chem       Date:  2017-01-23       Impact factor: 24.427

3.  Enantioselective synthesis of atropisomeric benzamides through peptide-catalyzed bromination.

Authors:  Kimberly T Barrett; Scott J Miller
Journal:  J Am Chem Soc       Date:  2013-02-14       Impact factor: 15.419

4.  Bifunctional organocatalysts for the asymmetric synthesis of axially chiral benzamides.

Authors:  Ryota Miyaji; Yuuki Wada; Akira Matsumoto; Keisuke Asano; Seijiro Matsubara
Journal:  Beilstein J Org Chem       Date:  2017-08-02       Impact factor: 2.883

5.  Hydrogen-Bond-Enabled Dynamic Kinetic Resolution of Axially Chiral Amides Mediated by a Chiral Counterion.

Authors:  Alison J Fugard; Antti S K Lahdenperä; Jaqueline S J Tan; Aroonroj Mekareeya; Robert S Paton; Martin D Smith
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-06       Impact factor: 15.336

  5 in total

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