Literature DB >> 24861469

Direct asymmetric dearomatization of pyridines and pyrazines by iridium-catalyzed allylic amination reactions.

Ze-Peng Yang1, Qing-Feng Wu, Shu-Li You.   

Abstract

The first iridium-catalyzed intramolecular asymmetric allylic dearomatization reaction of pyridines and pyrazines has been realized. 2,3-Dihydroindolizine and 6,7-dihydropyrrolo[1,2-a]pyrazine derivatives were obtained with excellent yields and enantioselectivity. This methodology features dearomatization by direct N-allylic alkylation of pyridines or pyrazines under mild reaction conditions.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  allylic compounds; asymmetric catalysis; cyclization; heterocycles; iridium

Year:  2014        PMID： 24861469     DOI： 10.1002/anie.201404286

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


  13 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.  Enantioselective γ-Alkylation of α,β-Unsaturated Malonates and Ketoesters by a Sequential Ir-Catalyzed Asymmetric Allylic Alkylation/Cope Rearrangement.

Authors:  Wen-Bo Liu; Noriko Okamoto; Eric J Alexy; Allen Y Hong; Kristy Tran; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2016-04-18       Impact factor: 15.419

4.  Evidence for Simultaneous Dearomatization of Two Aromatic Rings under Mild Conditions in Cu(I)-Catalyzed Direct Asymmetric Dearomatization of Pyridine.

Authors:  Michael W Gribble; Richard Y Liu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2020-06-11       Impact factor: 15.419

5.  Iridium-Catalyzed Regio- and Enantioselective Allylic Substitution of Trisubstituted Allylic Electrophiles.

Authors:  Ming Chen; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2016-08-17       Impact factor: 15.336

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

Authors:  Arismel Tena Meza; Thomas Wurm; Lewis Smith; Seung Wook Kim; Jason R Zbieg; Craig E Stivala; Michael J Krische
Journal:  J Am Chem Soc       Date:  2018-01-19       Impact factor: 15.419

7.  Diastereoselective Synthesis of β-Lactams by Ligand-Controlled Stereodivergent Intramolecular Tsuji-Trost Allylation.

Authors:  Matteo Faltracco; Verena Sukowski; Max van Druenen; Trevor A Hamlin; F Matthias Bickelhaupt; Eelco Ruijter
Journal:  J Org Chem       Date:  2020-07-13       Impact factor: 4.354

8.  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

9.  Iridium-catalyzed regio- and enantioselective allylic substitution of silyl dienolates derived from dioxinones.

Authors:  Ming Chen; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-15       Impact factor: 15.336

10.  Enantioselective N-heterocyclic carbene-catalyzed nucleophilic dearomatization of alkyl pyridiniums.

Authors:  Darrin M Flanigan; Tomislav Rovis
Journal:  Chem Sci       Date:  2017-08-03       Impact factor: 9.825
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