Literature DB >> 30964961

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

Seung Wook Kim1, Tabitha T Schempp1, Jason R Zbieg2, Craig E Stivala2, Michael J Krische1.   

Abstract

Cyclometallated π-allyliridium C,O-benzoates modified with (S)-tol-BINAP, which are stable to air, water, and SiO2 , catalyze highly enantioselective N-allylations of indoles and related azoles. This reaction complements previously reported metal-catalyzed indole allylations in that complete levels of N versus C3 and branched versus linear regioselectivity are observed.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−N bond formation; allylic alkylation; amination; enantioselective reactions; iridium

Year:  2019        PMID： 30964961      PMCID： PMC6534432          DOI： 10.1002/anie.201902799

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


  78 in total

1.  Asymmetric Transition Metal-Catalyzed Allylic Alkylations.

Authors:  Barry M. Trost; David L. Van Vranken
Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

2.  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

3.  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

4.  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

5.  Iridium complex-catalyzed allylic amination of allylic esters.

Authors:  R Takeuchi; N Ue; K Tanabe; K Yamashita; N Shiga
Journal:  J Am Chem Soc       Date:  2001-10-03       Impact factor: 15.419

6.  Chemo-, regio-, and enantioselective Pd-catalyzed allylic alkylation of indolocarbazole pro-aglycons.

Authors:  Barry M Trost; Michael J Krische; Volker Berl; Ellen M Grenzer
Journal:  Org Lett       Date:  2002-06-13       Impact factor: 6.005

7.  Regio- and enantioselective iridium-catalysed allylic aminations and alkylations of dienyl esters.

Authors:  Gunter Lipowsky; Günter Helmchen
Journal:  Chem Commun (Camb)       Date:  2003-11-07       Impact factor: 6.222

8.  Editing the stereochemical elements in an iridium catalyst for enantioselective allylic amination.

Authors:  Andreas Leitner; Chutian Shu; John F Hartwig
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-05       Impact factor: 11.205

9.  Identification of an activated catalyst in the iridium-catalyzed allylic amination and etherification. Increased rates, scope, and selectivity.

Authors:  Christoph A Kiener; Chutian Shu; Christopher Incarvito; John F Hartwig
Journal:  J Am Chem Soc       Date:  2003-11-26       Impact factor: 15.419

10.  First intramolecular enantioselective iridium-catalysed allylic aminations.

Authors:  Carolin Welter; Oliver Koch; Gunter Lipowsky; Günter Helmchen
Journal:  Chem Commun (Camb)       Date:  2004-03-05       Impact factor: 6.222
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  5 in total

1.  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

2.  Photochemical Asymmetric Nickel-Catalyzed Acyl Cross-Coupling.

Authors:  Eugenio Gandolfo; Xinjun Tang; Sudipta Raha Roy; Paolo Melchiorre
Journal:  Angew Chem Int Ed Engl       Date:  2019-10-07       Impact factor: 15.336

3.  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 4.  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

5.  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
  5 in total

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