Literature DB >> 15686341

Axially chiral biaryl diols catalyze highly enantioselective hetero-Diels-Alder reactions through hydrogen bonding.

Aditya K Unni1, Norito Takenaka, Hisashi Yamamoto, Viresh H Rawal.   

Abstract

Axially chiral 1,1'-biaryl-2,2'-dimethanol (3, BAMOL) family of diols are highly effective catalysts for enantioselective hetero-Diels-Alder reactions between aminosiloxydiene 1 and a wide variety of unactivated aldehydes. The reactions proceed in useful yields and excellent enantioselectivities. The diols function in the same capacity as Lewis acids, by activating the aldehyde carbonyl group through hydrogen bonding.

Entities:  

Year:  2005        PMID： 15686341     DOI： 10.1021/ja044076x

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


  16 in total

1.  Hydrogen bond catalyzed enantioselective vinylogous Mukaiyama aldol reaction.

Authors:  Vijaya Bhasker Gondi; Michel Gravel; Viresh H Rawal
Journal:  Org Lett       Date:  2005-12-08       Impact factor: 6.005

2.  Asymmetric Diels-Alder reactions of 2-pyrones with a bifunctional organic catalyst.

Authors:  Yi Wang; Hongming Li; Yong-Qiang Wang; Yan Liu; Bruce M Foxman; Li Deng
Journal:  J Am Chem Soc       Date:  2007-05-01       Impact factor: 15.419

3.  Hydrogen bonding catalysis operates by charge stabilization in highly polar Diels-Alder reactions.

Authors:  Ruth Gordillo; Travis Dudding; Christopher D Anderson; K N Houk
Journal:  Org Lett       Date:  2007-02-01       Impact factor: 6.005

4.  Pyrones to pyrans: enantioselective radical additions to acyloxy pyrones.

Authors:  Mukund P Sibi; Jake Zimmerman
Journal:  J Am Chem Soc       Date:  2006-10-18       Impact factor: 15.419

5.  Selective N1/N4 1,4-Cycloaddition of 1,2,4,5-Tetrazines Enabled by Solvent Hydrogen Bonding.

Authors:  Zixi Zhu; Christopher M Glinkerman; Dale L Boger
Journal:  J Am Chem Soc       Date:  2020-11-30       Impact factor: 15.419

6.  Catalysis of Heterocyclic Azadiene Cycloaddition Reactions by Solvent Hydrogen Bonding: Concise Total Synthesis of Methoxatin.

Authors:  Christopher M Glinkerman; Dale L Boger
Journal:  J Am Chem Soc       Date:  2016-09-14       Impact factor: 15.419

7.  Diastereoselective and enantioselective synthesis of tertiary alpha-hydroxy phosphonates through hydrogen-bond catalysis.

Authors:  Vijaya Bhasker Gondi; Koji Hagihara; Viresh H Rawal
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

8.  Exploring the potential of diarylacetylenediols as hydrogen bonding catalysts.

Authors:  Yunus E Türkmen; Viresh H Rawal
Journal:  J Org Chem       Date:  2013-08-14       Impact factor: 4.354

9.  Iridium-Catalyzed Enantioselective Allylic Substitution of Enol Silanes from Vinylogous Esters and Amides.

Authors:  Ming Chen; John F Hartwig
Journal:  J Am Chem Soc       Date:  2015-10-23       Impact factor: 15.419

10.  Ten years of research in Chicago.

Authors:  Hisashi Yamamoto
Journal:  Tetrahedron       Date:  2013-06-10       Impact factor: 2.457
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