Literature DB >> 19708700

Highly enantioselective and organocatalytic alpha-amination of 2-oxindoles.

Liang Cheng1, Li Liu, Dong Wang, Yong-Jun Chen.   

Abstract

An effective method for the asymmetric synthesis of 3-amino-2-oxindoles was developed. The tetrasubstituted chiral carbon center was generated by asymmetric amination of N-unprotected 2-oxindoles with azodicarboxylate catalyzed by commercial biscinchona alkaloids in good to excellent yields with high enantioselectivities.

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Year:  2009        PMID： 19708700     DOI： 10.1021/ol901405r

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


  14 in total

1.  α-Amination of keto-nitrones via multihetero-Cope rearrangement employing an imidoyl chloride reagent.

Authors:  Justin T Malinowski; Ericka J Malow; Jeffrey S Johnson
Journal:  Chem Commun (Camb)       Date:  2012-06-26       Impact factor: 6.222

2.  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

3.  Chiral calcium VAPOL phosphate mediated asymmetric chlorination and Michael reactions of 3-substituted oxindoles.

Authors:  Wenhua Zheng; Zuhui Zhang; Matthew J Kaplan; Jon C Antilla
Journal:  J Am Chem Soc       Date:  2011-02-22       Impact factor: 15.419

4.  Asymmetric catalytic aza-Morita-Baylis-Hillman reaction for the synthesis of 3-substituted-3-aminooxindoles with chiral quaternary carbon centers.

Authors:  Fang-Le Hu; Yin Wei; Min Shi; Suresh Pindi; Guigen Li
Journal:  Org Biomol Chem       Date:  2013-02-13       Impact factor: 3.876

5.  Organocatalytic asymmetric allylic amination of Morita-Baylis-Hillman carbonates of isatins.

Authors:  Hang Zhang; Shan-Jun Zhang; Qing-Qing Zhou; Lin Dong; Ying-Chun Chen
Journal:  Beilstein J Org Chem       Date:  2012-08-06       Impact factor: 2.883

6.  Organocatalytic asymmetric Michael addition of unprotected 3-substituted oxindoles to 1,4-naphthoquinone.

Authors:  Jin-Sheng Yu; Feng Zhou; Yun-Lin Liu; Jian Zhou
Journal:  Beilstein J Org Chem       Date:  2012-08-23       Impact factor: 2.883

7.  Enantioselective addition of diphenyl phosphonate to ketimines derived from isatins catalyzed by binaphthyl-modified organocatalysts.

Authors:  Hee Seung Jang; Yubin Kim; Dae Young Kim
Journal:  Beilstein J Org Chem       Date:  2016-07-20       Impact factor: 2.883

8.  Identification of a novel 2-oxindole fluorinated derivative as in vivo antitumor agent for prostate cancer acting via AMPK activation.

Authors:  Alicia Bort; Sergio Quesada; Ágata Ramos-Torres; Marta Gargantilla; Eva María Priego; Sophie Raynal; Franck Lepifre; Jose M Gasalla; Nieves Rodriguez-Henche; Ana Castro; Inés Díaz-Laviada
Journal:  Sci Rep       Date:  2018-03-12       Impact factor: 4.379

9.  Asymmetric α-amination of 3-substituted oxindoles using chiral bifunctional phosphine catalysts.

Authors:  Qiao-Wen Jin; Zhuo Chai; You-Ming Huang; Gang Zou; Gang Zhao
Journal:  Beilstein J Org Chem       Date:  2016-04-15       Impact factor: 2.883

10.  Direct catalytic enantioselective amination of ketones for the formation of tri- and tetrasubstituted stereocenters.

Authors:  B M Trost; J S Tracy; T Saget
Journal:  Chem Sci       Date:  2018-02-14       Impact factor: 9.825
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