Literature DB >> 27305459

Detrifluoroacetylative in Situ Generation of Free 3-Fluoroindolin-2-one-Derived Tertiary Enolates: Design, Synthesis, and Assessment of Reactivity toward Asymmetric Mannich Reactions.

Chen Xie1, Lijun Zhang1, Wanxing Sha1, Vadim A Soloshonok2,3, Jianlin Han1, Yi Pan1.   

Abstract

The discovery of detrifluoroacetylative in situ generation of a new type of fluorinated amide enolates derived from 3-fluoroindolin-2-one and their asymmetric Mannich additions with sulfinylaldimines bearing fluoroalkyl groups is reported, which afforded α-fluoro-β-(fluoroalkyl)-β-aminoindolin-2-ones containing C-F quaternary stereogenic centers with excellent yields and high diastereoselectivities.

Entities:  

Year:  2016        PMID： 27305459     DOI： 10.1021/acs.orglett.6b01516

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


  8 in total

1.  Organocatalytic Stereoselective Synthesis of Fluorinated 3,3'-Linked Bisoxindoles.

Authors:  Max Moskowitz; Kaluvu Balaraman; Christian Wolf
Journal:  J Org Chem       Date:  2018-01-22       Impact factor: 4.354

2.  Organocatalytic Asymmetric Synthesis of α-Oxetanyl and α-Azetidinyl Tertiary Alkyl Fluorides and Chlorides.

Authors:  Ransheng Ding; Christian Wolf
Journal:  Org Lett       Date:  2018-01-23       Impact factor: 6.005

3.  Catalytic Enantioselective and Diastereoselective Allylic Alkylation with Fluoroenolates: Efficient Access to C3-Fluorinated and All-Carbon Quaternary Oxindoles.

Authors:  Kaluvu Balaraman; Christian Wolf
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-27       Impact factor: 15.336

4.  Stereoselective Synthesis of 3,3'-Bisindolines by Organocatalytic Michael Additions of Fluorooxindole Enolates to Isatylidene Malononitriles in Aqueous Solution.

Authors:  Kaluvu Balaraman; Ransheng Ding; Christian Wolf
Journal:  Adv Synth Catal       Date:  2017-09-22       Impact factor: 5.837

Review 5.  Modern Approaches for Asymmetric Construction of Carbon-Fluorine Quaternary Stereogenic Centers: Synthetic Challenges and Pharmaceutical Needs.

Authors:  Yi Zhu; Jianlin Han; Jiandong Wang; Norio Shibata; Mikiko Sodeoka; Vadim A Soloshonok; Jaime A S Coelho; F Dean Toste
Journal:  Chem Rev       Date:  2018-04-02       Impact factor: 60.622

Review 6.  Catalytic stereoselective Mannich-type reactions for construction of fluorinated compounds.

Authors:  Minoo Dabiri; Noushin Farajinia Lehi; Reza Mohammadian
Journal:  Mol Divers       Date:  2021-07-06       Impact factor: 2.943

7.  Asymmetric Mannich reactions of (S)-N-tert-butylsulfinyl-3,3,3-trifluoroacetaldimines with yne nucleophiles.

Authors:  Ziyi Li; Li Wang; Yunqi Huang; Haibo Mei; Hiroyuki Konno; Hiroki Moriwaki; Vadim A Soloshonok; Jianlin Han
Journal:  Beilstein J Org Chem       Date:  2020-10-29       Impact factor: 2.883

Review 8.  Detrifluoroacetylative in Situ Generated Cyclic Fluorinated Enolates for the Preparation of Compounds Featuring a C-F Stereogenic Center.

Authors:  Jiang Liu; Ziyi Li; Haibo Mei; Vadim A Soloshonok; Jianlin Han
Journal:  ACS Omega       Date:  2019-11-14
  8 in total

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