Literature DB >> 18642826

Organocatalytic stereoselective mannich reaction of 3-substituted oxindoles.

Xu Tian1, Kun Jiang, Jing Peng, Wei Du, Ying-Chun Chen.   

Abstract

The asymmetric Mannich reaction of 3-substituted oxindoles and N-Boc imines was investigated for the first time, employing bifunctional thiourea-tertiary amine organocatalysts based on DPEN scaffold. The novel transformations exhibited high diastereoselectivities, and the Mannich adducts bearing adjacent quaternary and tertiary chiral centers were generally obtained in good to excellent enantioselectivities (up to 95% ee).

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Year:  2008        PMID: 18642826     DOI: 10.1021/ol801351j

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


  10 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.  Highly enantioselective trapping of zwitterionic intermediates by imines.

Authors:  Huang Qiu; Ming Li; Li-Qin Jiang; Feng-Ping Lv; Li Zan; Chang-Wei Zhai; Michael P Doyle; Wen-Hao Hu
Journal:  Nat Chem       Date:  2012-07-29       Impact factor: 24.427

4.  Highly enantioselective Mannich reactions with α-aryl silyl ketene acetals and imines.

Authors:  Gregory T Notte; Jenny M Baxter Vu; James L Leighton
Journal:  Org Lett       Date:  2011-01-14       Impact factor: 6.005

5.  Proline Sulfonamide-Based Organocatalysis: Better Late than Never.

Authors:  Hua Yang; Rich G Carter
Journal:  Synlett       Date:  2010-09-01       Impact factor: 2.454

6.  Stereochemical evaluation of bis(phosphine) copper catalysts for the asymmetric alkylation of 3-bromooxindoles with α-arylated malonate esters.

Authors:  Chung Whan Lee; Seo-Jung Han; Scott C Virgil; Brian M Stoltz
Journal:  Tetrahedron       Date:  2015-06-03       Impact factor: 2.457

7.  Catalytic double stereoinduction in asymmetric allylic alkylation of oxindoles.

Authors:  Barry M Trost; Yong Zhang
Journal:  Chemistry       Date:  2010-01-04       Impact factor: 5.236

8.  Direct Catalytic Asymmetric Mannich Reactions for the Construction of Quaternary Carbon Stereocenters.

Authors:  Barry M Trost; Tanguy Saget; Chao-I Joey Hung
Journal:  J Am Chem Soc       Date:  2016-03-09       Impact factor: 15.419

9.  Palladium-catalyzed enantioselective alpha-arylation and alpha-vinylation of oxindoles facilitated by an axially chiral P-stereogenic ligand.

Authors:  Alexander M Taylor; Ryan A Altman; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-07-29       Impact factor: 15.419

10.  Chiral ammonium betaine-catalyzed asymmetric Mannich-type reaction of oxindoles.

Authors:  Masahiro Torii; Kohsuke Kato; Daisuke Uraguchi; Takashi Ooi
Journal:  Beilstein J Org Chem       Date:  2016-09-28       Impact factor: 2.883

  10 in total

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