Literature DB >> 22455439

Addition of indoles to oxyallyl cations for facile access to α-indole carbonyl compounds.

Qiang Tang1, Xingkuan Chen, Bhoopendra Tiwari, Yonggui Robin Chi.   

Abstract

A direct coupling of unprotected indoles and α-halo ketones via in situ generated oxyallyl cation intermediates is described. The reactions efficiently afford α-indole carbonyl compounds with good to quantitative yields.

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Year:  2012        PMID： 22455439     DOI： 10.1021/ol300591z

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


  6 in total

1.  Intercepted Retro-Nazarov Reaction: Syntheses of Amidino-Rocaglate Derivatives and Their Biological Evaluation as eIF4A Inhibitors.

Authors:  Wenhan Zhang; Jennifer Chu; Andrew M Cyr; Han Yueh; Lauren E Brown; Tony T Wang; Jerry Pelletier; John A Porco
Journal:  J Am Chem Soc       Date:  2019-07-30       Impact factor: 15.419

2.  Mechanistic Perspectives in the Regioselective Indole Addition to Unsymmetrical Silyloxyallyl Cations.

Authors:  Caitlin G Bresnahan; Kiara A Taylor-Edinbyrd; Alexander H Cleveland; Joshua A Malone; Nitin S Dange; Anne Milet; Revati Kumar; Rendy Kartika
Journal:  J Org Chem       Date:  2019-05-16       Impact factor: 4.354

3.  Oxy-Allyl Cation Catalysis: An Enantioselective Electrophilic Activation Mode.

Authors:  Chun Liu; E Zachary Oblak; Mark N Vander Wal; Andrew K Dilger; Danielle K Almstead; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2016-02-09       Impact factor: 15.419

4.  Cooperative benzylic-oxyallylic stabilized cations: regioselective construction of α-quaternary centers in ketone-derived compounds.

Authors:  Nitin S Dange; Jacob R Stepherson; Caitlan E Ayala; Frank R Fronczek; Rendy Kartika
Journal:  Chem Sci       Date:  2015-07-22       Impact factor: 9.825

5.  Development of an imidazole salt catalytic system for the preparation of bis(indolyl)methanes and bis(naphthyl)methane.

Authors:  Xu Wang; Courtney C Aldrich
Journal:  PLoS One       Date:  2019-04-25       Impact factor: 3.240

6.  Formal Enone α-Arylation via I(III)-Mediated Aryl Migration/Elimination.

Authors:  Bruna S Martins; Daniel Kaiser; Adriano Bauer; Irmgard Tiefenbrunner; Nuno Maulide
Journal:  Org Lett       Date:  2021-02-26       Impact factor: 6.005
  6 in total

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