Literature DB >> 21261277

Highly enantioselective Pd-catalyzed allylic alkylation of indoles using Sulfur-MOP ligand.

Takashi Hoshi1, Koji Sasaki, Shun Sato, Yuichi Ishii, Toshio Suzuki, Hisahiro Hagiwara.   

Abstract

The preparation of various (R)-Sulfur-MOP ligands with aryl and alkyl substituents on sulfur, and the application of these ligands to Pd-catalyzed asymmetric allylic alkylation of indoles is reported. The sulfur substituent served as an effective stereocontrol element, and in the case of the 2-i-PrPh substituent on sulfur, the allylation products from an array of simple and substituted indoles were obtained with high enantioselectivity (up to 95% ee).

Entities:  

Year:  2011        PMID: 21261277     DOI: 10.1021/ol102977b

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


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

Authors:  Thomas D Montgomery; Ye Zhu; Natsuko Kagawa; Viresh H Rawal
Journal:  Org Lett       Date:  2013-02-21       Impact factor: 6.005

3.  Rapid assembly of functionalised spirocyclic indolines by palladium-catalysed dearomatising diallylation of indoles with allyl acetate.

Authors:  Persis Dhankher; Laure Benhamou; Tom D Sheppard
Journal:  Chemistry       Date:  2014-08-29       Impact factor: 5.236

4.  Rapid access to spirocyclized indolenines via palladium-catalyzed cascade reactions of tryptamine derivatives and propargyl carbonate.

Authors:  Thomas D Montgomery; Antoinette E Nibbs; Ye Zhu; Viresh H Rawal
Journal:  Org Lett       Date:  2014-06-25       Impact factor: 6.005

5.  Rhodium-catalyzed asymmetric hydroamination and hydroindolation of keto-vinylidenecyclopropanes.

Authors:  Song Yang; Quan-Zhe Li; Chen Xu; Qin Xu; Min Shi
Journal:  Chem Sci       Date:  2018-05-11       Impact factor: 9.825

  5 in total

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