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Literature DB >> 20677752

Enantioselective construction of spiroindolenines by Ir-catalyzed allylic alkylation reactions.

Qing-Feng Wu¹, Hu He, Wen-Bo Liu, Shu-Li You.

Abstract

With 2-methyl-1,2,3,4-tetrahydroquinoline-derived phosphoramidite ligand (R,R(a))-L(6), Ir-catalyzed intramolecular C-3 allylic alkylation of indoles has been realized to afford highly enantioenriched spiroindolenine derivatives in 92-98% yields with up to >99/1 dr and 97% ee.

Entities: Chemical

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Year: 2010 PMID： 20677752 DOI： 10.1021/ja105111n

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

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Cited

17 in total

1. Palladium(0)-catalyzed arylative dearomatization of phenols.

Authors: Sophie Rousseaux; Jorge García-Fortanet; Miguel Angel Del Aguila Sanchez; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2011-05-25 Impact factor: 15.419

2. 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

3. 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

4. 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

5. Scope of the Reactions of Indolyl- and Pyrrolyl-Tethered N-Sulfonyl-1,2,3-triazoles: Rhodium(II)-Catalyzed Synthesis of Indole- and Pyrrole-Fused Polycyclic Compounds.

Authors: Liangbing Fu; Huw M L Davies
Journal: Org Lett Date: 2017-03-30 Impact factor: 6.005

10. Two-in-one strategy for fluorene-based spirocycles via Pd(0)-catalyzed spiroannulation of o-iodobiaryls with bromonaphthols.

Authors: Bojun Tan; Long Liu; Huayu Zheng; Tianyi Cheng; Dianhu Zhu; Xiaofeng Yang; Xinjun Luan
Journal: Chem Sci Date: 2020-09-08 Impact factor: 9.825

Enantioselective construction of spiroindolenines by Ir-catalyzed allylic alkylation reactions.

1. Palladium(0)-catalyzed arylative dearomatization of phenols.

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

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

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

5. Scope of the Reactions of Indolyl- and Pyrrolyl-Tethered N-Sulfonyl-1,2,3-triazoles: Rhodium(II)-Catalyzed Synthesis of Indole- and Pyrrole-Fused Polycyclic Compounds.

6. Palladium-Catalyzed Dearomative syn-1,4-Carboamination with Grignard Reagents.

7. Enantio-, diastereo-, and regioselective iridium-catalyzed asymmetric allylic alkylation of acyclic β-ketoesters.

8. Iridium-Catalyzed Enantioselective Allylic Substitution of Enol Silanes from Vinylogous Esters and Amides.

9. Iridium-catalyzed regioselective and enantioselective allylation of trimethylsiloxyfuran.

10. Two-in-one strategy for fluorene-based spirocycles via Pd(0)-catalyzed spiroannulation of o-iodobiaryls with bromonaphthols.