Literature DB >> 25346494

Metal-free enantioselective electrophilic activation of allenamides: stereoselective dearomatization of indoles.

Ciro Romano1, Minqiang Jia, Magda Monari, Elisabetta Manoni, Marco Bandini.   

Abstract

The effective and unprecedented chiral BINOL phosphoric acid catalyzed (1-10 mol%) dearomatization of indoles through electrophilic activation of allenamides (ee up to 94%), is documented. Besides the synthesis of 3,3-disubstituted indolenine cores, a dearomatization/hydrogen transfer cascade sequence is also presented as a new synthetic shortcut toward highly enantiomerically enriched indolines.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Brønsted acids; dearomatization; enantioselectivity; homogeneous catalysis; indoles

Year:  2014        PMID： 25346494     DOI： 10.1002/anie.201407518

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  8 in total

1.  Enantioselective Functionalization of Enamides at the β-Carbon Center with Indoles.

Authors:  Mirza A Saputra; Binod Nepal; Nitin S Dange; Pu Du; Frank R Fronczek; Revati Kumar; Rendy Kartika
Journal:  Angew Chem Int Ed Engl       Date:  2018-10-23       Impact factor: 15.336

2.  Synthesis of 3,3'-Disubstituted Indolenines Utilizing the Lewis Acid Catalyzed Alkylation of 2,3-Disubstituted Indoles with Trichloroacetimidates.

Authors:  Arijit A Adhikari; Léa Radal; John D Chisholm
Journal:  Synlett       Date:  2017-07-11       Impact factor: 2.454

3.  Asymmetric addition of α-branched cyclic ketones to allenamides catalyzed by a chiral phosphoric acid.

Authors:  Xiaoyu Yang; F Dean Toste
Journal:  Chem Sci       Date:  2016-01-19       Impact factor: 9.825

4.  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

5.  Dialkylation of Indoles with Trichloroacetimidates to Access 3,3-Disubstituted Indolenines.

Authors:  Tamie Suzuki; Nilamber A Mate; Arijit A Adhikari; John D Chisholm
Journal:  Molecules       Date:  2019-11-15       Impact factor: 4.411

6.  Total synthesis of (+)-spiroindimicin A and congeners unveils their antiparasitic activity.

Authors:  Zhen Zhang; Sneha Ray; Leah Imlay; Lauren T Callaghan; Hanspeter Niederstrasser; Prema Latha Mallipeddi; Bruce A Posner; Dawn M Wetzel; Margaret A Phillips; Myles W Smith
Journal:  Chem Sci       Date:  2021-06-30       Impact factor: 9.825

Review 7.  Chiral Phosphoric Acids as Versatile Tools for Organocatalytic Asymmetric Transfer Hydrogenations.

Authors:  Ádám Márk Pálvölgyi; Fabian Scharinger; Michael Schnürch; Katharina Bica-Schröder
Journal:  European J Org Chem       Date:  2021-10-14

8.  Asymmetric construction of acyclic quaternary stereocenters via direct enantioselective additions of α-alkynyl ketones to allenamides.

Authors:  Jiawen Wang; Faqian He; Xiaoyu Yang
Journal:  Nat Commun       Date:  2021-11-18       Impact factor: 14.919
  8 in total

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