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Literature DB >> 19431168

Enantioselective addition of boronates to acyl imines catalyzed by chiral biphenols.

Joshua A Bishop¹, Sha Lou, Scott E Schaus.

Abstract

On the big screen: A chiral biphenol catalyst screening protocol was developed for the rapid identification of enantioselective nucleophilic boronate reactions with acyl imines (see scheme). The approach successfully identified a unique catalyst for the reaction of aryl, vinyl, and alkynyl boronates. Mechanistic studies demonstrate boronate ligand exchange with the catalyst is necessary for activation towards nucleophilic addition.

Entities: Chemical Disease Gene

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Year: 2009 PMID： 19431168 PMCID： PMC2819183 DOI： 10.1002/anie.200901023

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

25 in total

1. Asymmetric, catalytic phenyl transfer to imines: highly enantioselective synthesis of diarylmethylamines.

Authors: Nina Hermanns; Stefan Dahmen; Carsten Bolm; Stefan Bräse
Journal: Angew Chem Int Ed Engl Date: 2002-10-04 Impact factor: 15.336

2. Privileged chiral catalysts.

Authors: Tehshik P Yoon; Eric N Jacobsen
Journal: Science Date: 2003-03-14 Impact factor: 47.728

3. Catalytic enantioselective indium-mediated allylation of hydrazones.

Authors: Gregory R Cook; Robert Kargbo; Bikash Maity
Journal: Org Lett Date: 2005-06-23 Impact factor: 6.005

4. Readily accessible, modular, and tuneable BINOL 3,3'-perfluoroalkylsulfones: highly efficient catalysts for enantioselective in-mediated imine allylation.

Authors: Robert Kargbo; Yoko Takahashi; Santosh Bhor; Gregory R Cook; Guy C Lloyd-Jones; Ian R Shepperson
Journal: J Am Chem Soc Date: 2007-03-13 Impact factor: 15.419

5. A ligand-library approach to the highly efficient rhodium/phosphoramidite-catalyzed asymmetric arylation of N,N-dimethylsulfamoyl-protected aldimines.

Authors: Richard B C Jagt; Patrick Y Toullec; Danny Geerdink; Johannes G de Vries; Ben L Feringa; Adriaan J Minnaard
Journal: Angew Chem Int Ed Engl Date: 2006-04-21 Impact factor: 15.336

Review 6. Synergistic effect of binary component ligands in chiral catalyst library engineering for enantioselective reactions.

Authors: Kuiling Ding
Journal: Chem Commun (Camb) Date: 2008-01-21 Impact factor: 6.222

7. C2-symmetric bicyclo[2.2.2]octadienes as chiral ligands: their high performance in rhodium-catalyzed asymmetric arylation of N-tosylarylimines.

Authors: Norihito Tokunaga; Yusuke Otomaru; Kazuhiro Okamoto; Kazuhito Ueyama; Ryo Shintani; Tamio Hayashi
Journal: J Am Chem Soc Date: 2004-10-27 Impact factor: 15.419

8. Synthesis and applications of chiral organoboranes generated from sulfonium ylides.

Authors: Varinder K Aggarwal; Guang Yu Fang; Andreas T Schmidt
Journal: J Am Chem Soc Date: 2005-02-16 Impact factor: 15.419

9. Asymmetric allylboration of acyl imines catalyzed by chiral diols.

Authors: Sha Lou; Philip N Moquist; Scott E Schaus
Journal: J Am Chem Soc Date: 2007-11-17 Impact factor: 15.419

10. Asymmetric synthesis of diarylmethyl amines by rhodium-catalyzed asymmetric addition of aryl titanium reagents to imines.

Authors: Tamio Hayashi; Masahiro Kawai; Norihito Tokunaga
Journal: Angew Chem Int Ed Engl Date: 2004-11-19 Impact factor: 15.336

8 in total

Enantioselective addition of boronates to acyl imines catalyzed by chiral biphenols.

1. Asymmetric, catalytic phenyl transfer to imines: highly enantioselective synthesis of diarylmethylamines.

2. Privileged chiral catalysts.

3. Catalytic enantioselective indium-mediated allylation of hydrazones.

4. Readily accessible, modular, and tuneable BINOL 3,3'-perfluoroalkylsulfones: highly efficient catalysts for enantioselective in-mediated imine allylation.

5. A ligand-library approach to the highly efficient rhodium/phosphoramidite-catalyzed asymmetric arylation of N,N-dimethylsulfamoyl-protected aldimines.

Review 6. Synergistic effect of binary component ligands in chiral catalyst library engineering for enantioselective reactions.

7. C2-symmetric bicyclo[2.2.2]octadienes as chiral ligands: their high performance in rhodium-catalyzed asymmetric arylation of N-tosylarylimines.

8. Synthesis and applications of chiral organoboranes generated from sulfonium ylides.

9. Asymmetric allylboration of acyl imines catalyzed by chiral diols.

10. Asymmetric synthesis of diarylmethyl amines by rhodium-catalyzed asymmetric addition of aryl titanium reagents to imines.

1. Enantioselective addition of boronates to chromene acetals catalyzed by a chiral Brønsted acid/Lewis acid system.

2. Asymmetric propargylation of ketones using allenylboronates catalyzed by chiral biphenols.

3. Enantioselective Synthesis of Allenes by Catalytic Traceless Petasis Reactions.

4. Asymmetric Petasis Borono-Mannich Allylation Reactions Catalyzed by Chiral Biphenols.

5. Asymmetric Traceless Petasis Borono-Mannich Reactions of Enals: Reductive Transposition of Allylic Diazenes.

6. Enantioselective addition of boronates to o-quinone methides catalyzed by chiral biphenols.

7. Reactivity and Synthetic Applications of Multicomponent Petasis Reactions.

Review 8. Chiral Diol-Based Organocatalysts in Enantioselective Reactions.