Literature DB >> 14737515

Atropisomers and near-atropisomers: achieving stereoselectivity by exploiting the conformational preferences of aromatic amides.

Jonathan Clayden1.   

Abstract

The conformational preferences of aromatic amides are remarkably easy to control with a high degree of selectivity. This article reviews the consequences of this unusual form of stereocontrol, which enables for example the asymmetric synthesis of atropisomers and the ability to achieve remote stereocontrol by conformational relay.

Entities:  

Year:  2003        PMID： 14737515     DOI： 10.1039/b307976g

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  11 in total

1.  Towards a Catalytic Atroposelective Synthesis of Diaryl Ethers via C(sp 2)-H Alkylation Using Nitroalkanes.

Authors:  Andrew N Dinh; Ryan R Noorbehesht; Sean T Toenjes; Amy C Jackson; Mirza A Saputra; Sean M Maddox; Jeffrey L Gustafson
Journal:  Synlett       Date:  2018-07-31       Impact factor: 2.454

2.  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

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.  Enantioselective Synthesis of Pyrrolopyrimidine Scaffolds through Cation-Directed Nucleophilic Aromatic Substitution.

Authors:  Mariel M Cardenas; Sean T Toenjes; Christopher J Nalbandian; Jeffrey L Gustafson
Journal:  Org Lett       Date:  2018-03-21       Impact factor: 6.005

5.  Atropisomerism in the Pharmaceutically Relevant Realm.

Authors:  Mariami Basilaia; Matthew H Chen; Jim Secka; Jeffrey L Gustafson
Journal:  Acc Chem Res       Date:  2022-09-26       Impact factor: 24.466

6.  Synthesis of enantiomerically enriched (R)-C-labelled 2-aminoisobutyric acid (Aib) by conformational memory in the alkylation of a derivative of L-alanine.

Authors:  Stephen P Fletcher; Jordi Solà; Dean Holt; Robert A Brown; Jonathan Clayden
Journal:  Beilstein J Org Chem       Date:  2011-09-20       Impact factor: 2.883

7.  Asymmetric synthesis of biaryl atropisomers by dynamic resolution on condensation of biaryl aldehydes with (-)-ephedrine or a proline-derived diamine.

Authors:  Ann Bracegirdle; Jonathan Clayden; Lai Wah Lai
Journal:  Beilstein J Org Chem       Date:  2008-12-04       Impact factor: 2.883

8.  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

9.  Atropisomerism in Diarylamines: Structural Requirements and Mechanisms of Conformational Interconversion.

Authors:  Romain Costil; Alistair J Sterling; Fernanda Duarte; Jonathan Clayden
Journal:  Angew Chem Int Ed Engl       Date:  2020-08-20       Impact factor: 16.823

10.  Atroposelective synthesis of N-aryl peptoid atropisomers via a palladium(ii)-catalyzed asymmetric C-H alkynylation strategy.

Authors:  Yong-Jie Wu; Pei-Pei Xie; Gang Zhou; Qi-Jun Yao; Xin Hong; Bing-Feng Shi
Journal:  Chem Sci       Date:  2021-06-09       Impact factor: 9.825
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