Literature DB >> 18582078

Enantioselective synthesis of 3,3-disubstituted oxindoles through Pd-catalyzed cyanoamidation.

Yoshizumi Yasui1, Haruhi Kamisaki, Yoshiji Takemoto.   

Abstract

The first enantioselective cyanoamidation of olefins provides quick access to a variety of 3,3-disubstituted oxindoles. The combination of Pd(dba)2, an optically active phosphoramidite, and N, N-dimethylpropylene urea (DMPU) in decalin were found to be the best conditions.

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Year:  2008        PMID： 18582078     DOI： 10.1021/ol801168j

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


  23 in total

1.  The palladium catalyzed asymmetric addition of oxindoles and allenes: an atom-economical versatile method for the construction of chiral indole alkaloids.

Authors:  Barry M Trost; Jia Xie; Joshua D Sieber
Journal:  J Am Chem Soc       Date:  2011-11-30       Impact factor: 15.419

2.  Alpha-arylation of 3-aryloxindoles.

Authors:  Cheng-Kang Mai; Matthew F Sammons; Tarek Sammakia
Journal:  Org Lett       Date:  2010-05-21       Impact factor: 6.005

3.  A General and Practical Palladium-Catalyzed Direct α-Arylation of Amides with Aryl Halides.

Authors:  Bing Zheng; Tiezheng Jia; Patrick J Walsh
Journal:  Adv Synth Catal       Date:  2014-01-13       Impact factor: 5.837

4.  Palladium catalyzed intramolecular acylcyanation of alkenes using α-iminonitriles.

Authors:  Naveen R Rondla; Jodi M Ogilvie; Zhongda Pan; Christopher J Douglas
Journal:  Chem Commun (Camb)       Date:  2014-08-18       Impact factor: 6.222

5.  Diastereoselective Intramolecular Cyanoamidation with Alkenes.

Authors:  Ashley M Dreis; Sadie C Otte; Matthew S Eastwood; Elizabeth R Alonzi; Jason T Brethorst; Christopher J Douglas
Journal:  European J Org Chem       Date:  2016-12-13

6.  Studies towards the total synthesis of drimentine C. Preparation of the AB and CDEF ring fragments.

Authors:  Sarah M Pound; Steven J Underwood; Christopher J Douglas
Journal:  European J Org Chem       Date:  2020-03-19

7.  Ethylene in organic synthesis: a new route to anticholenergic pyrrolidinoindolines, and other molecules with all carbon-quaternary centers via asymmetric hydrovinylation.

Authors:  Hwan Jung Lim; T V RajanBabu
Journal:  Org Lett       Date:  2011-11-21       Impact factor: 6.005

8.  Mechanistic Model for Enantioselective Intramolecular Alkene Cyanoamidation via Palladium-Catalyzed C-CN Bond Activation.

Authors:  Grant B Frost; Nicholas A Serratore; Jodi M Ogilvie; Christopher J Douglas
Journal:  J Org Chem       Date:  2017-03-15       Impact factor: 4.354

9.  Recent developments in the catalytic, asymmetric construction of pyrroloindolines bearing all-carbon quaternary stereocenters.

Authors:  Lindsay M Repka; Sarah E Reisman
Journal:  J Org Chem       Date:  2013-12-02       Impact factor: 4.354

10.  Asymmetric intramolecular arylcyanation of unactivated olefins via C-CN bond activation.

Authors:  Mary P Watson; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2008-08-30       Impact factor: 15.419
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