Literature DB >> 25947253

Asymmetric synthesis of quaternary α-fluoro-β-keto-amines via detrifluoroacetylative Mannich reactions.

Chen Xie1, Yanling Dai, Haibo Mei, Jianlin Han, Vadim A Soloshonok, Yi Pan.   

Abstract

Efficient asymmetric detrifluoroacetylative Mannich addition reactions between 2-fluoro-1,3-di-ketones/hydrates and chiral N-sulfinyl-imines via C-C bond cleavage were reported, which afforded C-F quaternary α-fluoro-β-keto-amines with excellent yields and high diastereoselectivity.

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Year:  2015        PMID： 25947253     DOI： 10.1039/c5cc02256h

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  10 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 Asymmetric Mannich Reaction of α-Fluoronitriles with Ketimines: Enantioselective and Diastereodivergent Construction of Vicinal Tetrasubstituted Stereocenters.

Authors:  Ransheng Ding; Zeus A De Los Santos; Christian Wolf
Journal:  ACS Catal       Date:  2019-02-06       Impact factor: 13.084

4.  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

5.  Catalytic Asymmetric Allylic Alkylation with Arylfluoroacetonitriles.

Authors:  Archita Sripada; Christian Wolf
Journal:  J Org Chem       Date:  2022-08-17       Impact factor: 4.198

6.  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

7.  Detrifluoroacetylative Generation of Halogenated Enolates: Practical Access to Perhalogenated Ketones and Alkenes.

Authors:  Kaluvu Balaraman; Max Moskowitz; Yang Liu; Christian Wolf
Journal:  Synthesis (Stuttg)       Date:  2016-04-20       Impact factor: 3.157

Review 8.  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

9.  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 10.  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
  10 in total

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