Literature DB >> 24079481

Electrophilic rearrangements of chiral amides: a traceless asymmetric α-allylation.

Bo Peng1, Danny Geerdink, Nuno Maulide.   

Abstract

A one-pot protocol for the asymmetric α-allylation reaction is reported relying on a key efficient asymmetric Claisen rearrangement, triggered by electrophilic activation of chiral pseudoephedrine amides. Subsequent reduction or hydrolysis of the resulting iminium ions provides highly enantioenriched α-allylic aldehydes or carboxylic acids in a traceless manner. Compared to traditional alternatives which make use of strongly basic conditions, the work presented herein displays unprecedented functional group tolerance.

Entities:  

Year:  2013        PMID： 24079481     DOI： 10.1021/ja408856p

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


  13 in total

1.  Activation of C-O and C-N Bonds Using Non-Precious-Metal Catalysis.

Authors:  Timothy B Boit; Ana S Bulger; Jacob E Dander; Neil K Garg
Journal:  ACS Catal       Date:  2020-09-10       Impact factor: 13.084

2.  Direct Observation of Intermediates Involved in the Interruption of the Bischler-Napieralski Reaction.

Authors:  Kolby L White; Marius Mewald; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2015-07-22       Impact factor: 4.354

3.  Mechanistic Pathways in Amide Activation: Flexible Synthesis of Oxazoles and Imidazoles.

Authors:  Giovanni Di Mauro; Boris Maryasin; Daniel Kaiser; Saad Shaaban; Leticia González; Nuno Maulide
Journal:  Org Lett       Date:  2017-07-13       Impact factor: 6.005

4.  Enantioselective Allenoate-Claisen Rearrangement Using Chiral Phosphate Catalysts.

Authors:  Javier Miró; Tobias Gensch; Mario Ellwart; Seo-Jung Han; Hsin-Hui Lin; Matthew S Sigman; F Dean Toste
Journal:  J Am Chem Soc       Date:  2020-03-23       Impact factor: 15.419

5.  Uniting Amide Synthesis and Activation by PIII/PV-Catalyzed Serial Condensation: Three-Component Assembly of 2-Amidopyridines.

Authors:  Jeffrey M Lipshultz; Alexander T Radosevich
Journal:  J Am Chem Soc       Date:  2021-09-03       Impact factor: 16.383

6.  Chemo- and Stereoselective Transition-Metal-Free Amination of Amides with Azides.

Authors:  Veronica Tona; Aurélien de la Torre; Mohan Padmanaban; Stefan Ruider; Leticia González; Nuno Maulide
Journal:  J Am Chem Soc       Date:  2016-06-28       Impact factor: 15.419

7.  Direct Regioselective Synthesis of Tetrazolium Salts by Activation of Secondary Amides under Mild Conditions.

Authors:  Veronica Tona; Boris Maryasin; Aurélien de la Torre; Josefine Sprachmann; Leticia González; Nuno Maulide
Journal:  Org Lett       Date:  2017-05-09       Impact factor: 6.005

8.  Chiral Fe(ii) complex catalyzed enantioselective [1,3] O-to-C rearrangement of alkyl vinyl ethers and synthesis of chromanols and beyond.

Authors:  Lifeng Wang; Pengfei Zhou; Qianchi Lin; Shunxi Dong; Xiaohua Liu; Xiaoming Feng
Journal:  Chem Sci       Date:  2020-09-07       Impact factor: 9.825

9.  Harnessing the Electrophilicity of Keteniminium Ions: A Simple and Straightforward Entry to Tetrahydropyridines and Piperidines from Ynamides.

Authors:  Morgan Lecomte; Gwilherm Evano
Journal:  Angew Chem Int Ed Engl       Date:  2016-03-02       Impact factor: 15.336

10.  Direct Synthesis of Enamides via Electrophilic Activation of Amides.

Authors:  Philipp Spieß; Martin Berger; Daniel Kaiser; Nuno Maulide
Journal:  J Am Chem Soc       Date:  2021-07-07       Impact factor: 15.419
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.