Literature DB >> 22335367

Enantioselective gold-catalyzed synthesis of polycyclic indolines.

Gianpiero Cera1, Michel Chiarucci, Andrea Mazzanti, Michele Mancinelli, Marco Bandini.   

Abstract

The synthesis of architecturally complex polycyclic fused indolines is achieved in a chemo-, regio-, and stereodefined manner, via an enantioselective gold-catalyzed cascade hydroindolination/iminium trapping synthetic sequence. Highly functionalized tetracyclic fused furoindolines (2) and dihydropyranylindolines (4) are synthesized in moderate to good yields and enantiomeric excesses of up to 87%.
© 2012 American Chemical Society

Entities:  

Year:  2012        PMID： 22335367     DOI： 10.1021/ol300297t

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


  11 in total

1.  Gold(I)-catalyzed enantioselective carboalkoxylation of alkynes.

Authors:  Weiwei Zi; F Dean Toste
Journal:  J Am Chem Soc       Date:  2013-08-19       Impact factor: 15.419

2.  Chiral anion phase transfer of aryldiazonium cations: an enantioselective synthesis of C3-diazenated pyrroloindolines.

Authors:  Hosea M Nelson; Solomon H Reisberg; Hunter P Shunatona; Jigar S Patel; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2014-04-08       Impact factor: 15.336

3.  Enantioselective Tandem Cyclization of Alkyne-Tethered Indoles Using Cooperative Silver(I)/Chiral Phosphoric Acid Catalysis.

Authors:  Yugen Zhu; Wei He; Wei Wang; Chloe E Pitsch; Xiaotai Wang; Xiang Wang
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-23       Impact factor: 15.336

4.  Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity.

Authors:  Ruth Dorel; Antonio M Echavarren
Journal:  Chem Rev       Date:  2015-04-06       Impact factor: 60.622

5.  Post-Ugi gold-catalyzed diastereoselective domino cyclization for the synthesis of diversely substituted spiroindolines.

Authors:  Amit Kumar; Dipak D Vachhani; Sachin G Modha; Sunil K Sharma; Virinder S Parmar; Erik V Van der Eycken
Journal:  Beilstein J Org Chem       Date:  2013-10-14       Impact factor: 2.883

6.  Ligand-enabled Ir-catalyzed intermolecular diastereoselective and enantioselective allylic alkylation of 3-substituted indoles.

Authors:  Xiao Zhang; Wen-Bo Liu; Hang-Fei Tu; Shu-Li You
Journal:  Chem Sci       Date:  2015-06-08       Impact factor: 9.825

7.  Highly efficient synthesis and stereoselective migration reactions of chiral five-membered aza-spiroindolenines: scope and mechanistic understanding.

Authors:  Qing-Feng Wu; Chao Zheng; Chun-Xiang Zhuo; Shu-Li You
Journal:  Chem Sci       Date:  2016-03-29       Impact factor: 9.825

8.  Construction of spirocarbocycles via gold-catalyzed intramolecular dearomatization of naphthols.

Authors:  Wen-Ting Wu; Ren-Qi Xu; Liming Zhang; Shu-Li You
Journal:  Chem Sci       Date:  2016-02-02       Impact factor: 9.825

9.  Modular Synthesis of Polycyclic Alkaloid Scaffolds via an Enantioselective Dearomative Cascade.

Authors:  James A Rossi-Ashton; Aimee K Clarke; Richard J K Taylor; William P Unsworth
Journal:  Org Lett       Date:  2020-01-15       Impact factor: 6.005

Review 10.  Recent Advances in Construction of Polycyclic Natural Product Scaffolds via One-Pot Reactions Involving Alkyne Annulation.

Authors:  Liyao Zheng; Ruimao Hua
Journal:  Front Chem       Date:  2020-10-15       Impact factor: 5.221
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