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Literature DB >> 18386906

Ir-catalyzed regio- and enantioselective Friedel-Crafts-type allylic alkylation of indoles.

Wen-Bo Liu¹, Hu He, Li-Xin Dai, Shu-Li You.

Abstract

Highly regio- and enantioselective Ir-catalyzed Friedel-Crafts type allylic alkylation of indoles have been realized using [Ir(COD)Cl]2/phosphoramidite ligand 1a, affording the branched products with up to >97/3 branched-linear ratio and 92% ee.

Entities: Chemical

Mesh：

Substances：
Indoles
Iridium

Year: 2008 PMID： 18386906 DOI： 10.1021/ol800409d

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

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. 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

3. Friedel-Crafts Alkylation of Indoles with Trichloroacetimidates.

Authors: Tamie Suzuki; John D Chisholm
Journal: Tetrahedron Lett Date: 2019-04-03 Impact factor: 2.415

4. 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

5. Construction of vicinal tertiary and all-carbon quaternary stereocenters via Ir-catalyzed regio-, diastereo-, and enantioselective allylic alkylation and applications in sequential Pd catalysis.

Authors: Wen-Bo Liu; Corey M Reeves; Scott C Virgil; Brian M Stoltz
Journal: J Am Chem Soc Date: 2013-07-12 Impact factor: 15.419

Ir-catalyzed regio- and enantioselective Friedel-Crafts-type allylic alkylation of indoles.

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

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

3. Friedel-Crafts Alkylation of Indoles with Trichloroacetimidates.

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

5. Construction of vicinal tertiary and all-carbon quaternary stereocenters via Ir-catalyzed regio-, diastereo-, and enantioselective allylic alkylation and applications in sequential Pd catalysis.

6. Alkyne Hydroheteroarylation: Enantioselective Coupling of Indoles and Alkynes via Rh-Hydride Catalysis.

7. Iridium-catalyzed kinetic asymmetric transformations of racemic allylic benzoates.

8. Palladium-catalyzed decarboxylative allylation and benzylation of N-alloc and N-Cbz indoles.

9. Iridium-catalyzed regio- and enantioselective N-allylation of indoles.

10. Asymmetric synthesis of N-allylic indoles via regio- and enantioselective allylation of aryl hydrazines.