Literature DB >> 29350523

Amphiphilic π-Allyliridium C,O-Benzoates Enable Regio- and Enantioselective Amination of Branched Allylic Acetates Bearing Linear Alkyl Groups.

Arismel Tena Meza1, Thomas Wurm2, Lewis Smith1, Seung Wook Kim2, Jason R Zbieg1, Craig E Stivala1, Michael J Krische2.   

Abstract

The first examples of amphiphilic reactivity in the context of enantioselective catalysis are described. Commercially available π-allyliridium C,O-benzoates, which are stable to air, water and SiO2 chromatography, and are well-known to catalyze allyl acetate-mediated carbonyl allylation, are now shown to catalyze highly chemo-, regio- and enantioselective substitutions of branched allylic acetates bearing linear alkyl groups with primary amines.

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Year:  2018        PMID： 29350523      PMCID： PMC6262838          DOI： 10.1021/jacs.7b13482

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


  60 in total

1.  Regio- and enantioselective allylic amination of achiral allylic esters catalyzed by an iridium-phosphoramidite complex.

Authors:  Toshimichi Ohmura; John F Hartwig
Journal:  J Am Chem Soc       Date:  2002-12-25       Impact factor: 15.419

2.  Pd-catalyzed enantioselective allylic substitution: new strategic options for the total synthesis of natural products.

Authors:  Timm Graening; Hans-Günther Schmalz
Journal:  Angew Chem Int Ed Engl       Date:  2003-06-16       Impact factor: 15.336

3.  Asymmetric transition-metal-catalyzed allylic alkylations: applications in total synthesis.

Authors:  Barry M Trost; Matthew L Crawley
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

4.  Iridium-catalyzed synthesis of primary allylic amines from allylic alcohols: sulfamic acid as ammonia equivalent.

Authors:  Christian Defieber; Martin A Ariger; Patricia Moriel; Erick M Carreira
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

5.  Mechanistically driven development of iridium catalysts for asymmetric allylic substitution.

Authors:  John F Hartwig; Levi M Stanley
Journal:  Acc Chem Res       Date:  2010-09-28       Impact factor: 22.384

6.  A highly enantioselective allylic amination reaction using a commercially available chiral rhodium catalyst: resolution of racemic allylic carbonates.

Authors:  Derek C Vrieze; Garrett S Hoge; Perrine Z Hoerter; Jared T Van Haitsma; Brian M Samas
Journal:  Org Lett       Date:  2009-07-16       Impact factor: 6.005

7.  A new approach to functionalized spiropiperidines through tandem RCM and nitrogen-directed reactions.

Authors:  Andrew S Edwards; Robert A J Wybrow; Craig Johnstone; Harry Adams; Joseph P A Harrity
Journal:  Chem Commun (Camb)       Date:  2002-07-21       Impact factor: 6.222

8.  Synthesis of alpha,beta-unsaturated gamma-lactams via asymmetric iridium-catalysed allylic substitution.

Authors:  Stephanie Spiess; Carola Berthold; Robert Weihofen; Günter Helmchen
Journal:  Org Biomol Chem       Date:  2007-06-26       Impact factor: 3.876

9.  Rhodium-catalyzed dynamic kinetic asymmetric transformations of racemic tertiary allylic trichloroacetimidates with anilines.

Authors:  Jeffrey S Arnold; Hien M Nguyen
Journal:  J Am Chem Soc       Date:  2012-05-14       Impact factor: 15.419

10.  Transition metal catalyzed nucleophilic allylic substitution: activation of allylic alcohols via π-allylic species.

Authors:  Basker Sundararaju; Mathieu Achard; Christian Bruneau
Journal:  Chem Soc Rev       Date:  2012-05-10       Impact factor: 54.564
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  9 in total

1.  Regio- and Enantioselective Iridium-Catalyzed N-Allylation of Indoles and Related Azoles with Racemic Branched Alkyl-Substituted Allylic Acetates.

Authors:  Seung Wook Kim; Tabitha T Schempp; Jason R Zbieg; Craig E Stivala; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2019-05-06       Impact factor: 15.336

2.  Regio- and Enantioselective Iridium-Catalyzed Amination of Racemic Branched Alkyl-Substituted Allylic Acetates with Primary and Secondary Aromatic and Heteroaromatic Amines.

Authors:  Seung Wook Kim; Leyah A Schwartz; Jason R Zbieg; Craig E Stivala; Michael J Krische
Journal:  J Am Chem Soc       Date:  2018-12-20       Impact factor: 15.419

3.  Catalytic Asymmetric Allylic Amination with Isatins, Sulfonamides, Imides, Amines, and N-Heterocycles.

Authors:  Ciarán C Lynch; Kaluvu Balaraman; Christian Wolf
Journal:  Org Lett       Date:  2020-04-07       Impact factor: 6.005

4.  Hydroamination versus Allylic Amination in Iridium-Catalyzed Reactions of Allylic Acetates with Amines: 1,3-Aminoalcohols via Ester-Directed Regioselectivity.

Authors:  Seung Wook Kim; Thomas Wurm; Gilmar A Brito; Woo-Ok Jung; Jason R Zbieg; Craig E Stivala; Michael J Krische
Journal:  J Am Chem Soc       Date:  2018-07-10       Impact factor: 15.419

5.  Regio- and Enantioselective Iridium-Catalyzed Amination of Alkyl-Substituted Allylic Acetates with Secondary Amines.

Authors:  Woo-Ok Jung; Minjin Yoo; Madyson M Migliozzi; Jason R Zbieg; Craig E Stivala; Michael J Krische
Journal:  Org Lett       Date:  2021-12-14       Impact factor: 6.005

6.  Kinetic, ESI-CID-MS and Computational Studies of π-Allyliridium C,O-Benzoate-Catalyzed Allylic Amination: Understanding the Effect of Cesium Ion.

Authors:  Woo-Ok Jung; Binh Khanh Mai; Minjin Yoo; Samuel W J Shields; Jason R Zbieg; Craig E Stivala; Peng Liu; Michael J Krische
Journal:  ACS Catal       Date:  2022-03-08       Impact factor: 13.700

7.  Enantioselective Iridium-Catalyzed Allylation of Nitroalkanes: Entry to β-Stereogenic α-Quaternary Primary Amines.

Authors:  Woo-Ok Jung; Binh Khanh Mai; Brian J Spinello; Zachary J Dubey; Seung Wook Kim; Craig E Stivala; Jason R Zbieg; Peng Liu; Michael J Krische
Journal:  J Am Chem Soc       Date:  2021-06-21       Impact factor: 16.383

Review 8.  Allenes and Dienes as Chiral Allylmetal Pronucleophiles in Catalytic Enantioselective C=X Addition: Historical Perspective and State-of-The-Art Survey.

Authors:  Ming Xiang; Dana E Pfaffinger; Michael J Krische
Journal:  Chemistry       Date:  2021-07-29       Impact factor: 5.020

9.  Iridium-Catalyzed Enantioselective Intermolecular Indole C2-Allylation.

Authors:  James A Rossi-Ashton; Aimee K Clarke; James R Donald; Chao Zheng; Richard J K Taylor; William P Unsworth; Shu-Li You
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-11       Impact factor: 15.336
  9 in total

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