Literature DB >> 24000200

Enantioselective electrophilic trifluoromethylthiolation of β-ketoesters: a case of reactivity and selectivity bias for organocatalysis.

Xueqiang Wang1, Tao Yang, Xiaolin Cheng, Qilong Shen.   

Abstract

A chiral Lewis base or a phase-transfer catalyst (PTC) can mediate the highly enantioselective trifluoromethylthiolation of β-ketoesters with the previously developed SCF3 reagent. Reactions of indanone-derived β-ketoesters occurred with high yield and excellent enantioselectivity with quinine as catalyst. Reactions of tetralone- or 1-benzosuberone-derived β-ketoesters occurred with moderate to good enantioselectivity with a quinine-derived PTC.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric synthesis; fluorine; organocatalysis; quinine; trifluoromethylthiolation

Mesh：

Substances：

Year:  2013        PMID： 24000200     DOI： 10.1002/anie.201305075

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  10 in total

1.  Structural reevaluation of the electrophilic hypervalent iodine reagent for trifluoromethylthiolation supported by the crystalline sponge method for X-ray analysis.

Authors:  Ekaterina V Vinogradova; Peter Müller; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-17       Impact factor: 15.336

2.  Visible-Light-Induced, Copper-Catalyzed Three-Component Coupling of Alkyl Halides, Olefins, and Trifluoromethylthiolate to Generate Trifluoromethyl Thioethers.

Authors:  Jian He; Caiyou Chen; Gregory C Fu; Jonas C Peters
Journal:  ACS Catal       Date:  2018-10-31       Impact factor: 13.084

3.  Catalytic asymmetric trifluoromethylthiolation via enantioselective [2,3]-sigmatropic rearrangement of sulfonium ylides.

Authors:  Zhikun Zhang; Zhe Sheng; Weizhi Yu; Guojiao Wu; Rui Zhang; Wen-Dao Chu; Yan Zhang; Jianbo Wang
Journal:  Nat Chem       Date:  2017-06-05       Impact factor: 24.427

4.  Difluorocarbene-Derived Trifluoromethylthiolation and [(18)F]Trifluoromethylthiolation of Aliphatic Electrophiles.

Authors:  Jian Zheng; Lu Wang; Jin-Hong Lin; Ji-Chang Xiao; Steven H Liang
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-21       Impact factor: 15.336

Review 5.  Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin-Anh and Chelation-Control Models.

Authors:  Nicole D Bartolo; Jacquelyne A Read; Elizabeth M Valentín; K A Woerpel
Journal:  Chem Rev       Date:  2020-01-06       Impact factor: 60.622

Review 6.  Advances in catalytic enantioselective fluorination, mono-, di-, and trifluoromethylation, and trifluoromethylthiolation reactions.

Authors:  Xiaoyu Yang; Tao Wu; Robert J Phipps; F Dean Toste
Journal:  Chem Rev       Date:  2014-10-22       Impact factor: 60.622

Review 7.  Asymmetric Preparation of α-Quaternary Fluorinated β-keto Esters. Review.

Authors:  Albert Granados; Adelina Vallribera
Journal:  Molecules       Date:  2020-07-17       Impact factor: 4.411

8.  Enantioselective Bifunctional Ammonium Salt-Catalyzed Syntheses of 3-CF3S-, 3-RS-, and 3-F-Substituted Isoindolinones.

Authors:  Andreas Eitzinger; Jan Otevrel; Victoria Haider; Antonio Macchia; Antonio Massa; Kirill Faust; Bernhard Spingler; Albrecht Berkessel; Mario Waser
Journal:  Adv Synth Catal       Date:  2021-02-17       Impact factor: 5.837

Review 9.  Chiral phase-transfer catalysis in the asymmetric α-heterofunctionalization of prochiral nucleophiles.

Authors:  Johannes Schörgenhumer; Maximilian Tiffner; Mario Waser
Journal:  Beilstein J Org Chem       Date:  2017-08-22       Impact factor: 2.883

10.  Selenide-catalyzed enantioselective synthesis of trifluoromethylthiolated tetrahydronaphthalenes by merging desymmetrization and trifluoromethylthiolation.

Authors:  Jie Luo; Qingxiang Cao; Xiaohui Cao; Xiaodan Zhao
Journal:  Nat Commun       Date:  2018-02-06       Impact factor: 14.919
  10 in total

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