Literature DB >> 11073679

Design, synthesis, and evaluation of a novel class of enantioselective electrophilic fluorinating agents: N-fluoro ammonium salts of cinchona alkaloids (F-CA-BF(4)).

D Cahard1, C Audouard, J C Plaquevent, N Roques.   

Abstract

The first enantiopure N-fluoro quaternary ammonium salts of cinchona alkaloids as enantioselective fluorinating agents are reported. A one-step transfer-fluorination on the naturally occurring cinchona alkaloids gave the fluorinating agents F-CA-BF(4). This new generation of fluorinating agents exhibited asymmetric induction up to 61% on fluorination of enolates and silyl enol ethers of 2-methyl-1-tetralone.

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Year:  2000        PMID： 11073679     DOI： 10.1021/ol006610l

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


  16 in total

1.  Alpha-olefins as alkenylmetal equivalents in catalytic conjugate addition reactions.

Authors:  Chun-Yu Ho; Hirohisa Ohmiya; Timothy F Jamison
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

Review 2.  Transition metal-catalyzed decarboxylative allylation and benzylation reactions.

Authors:  Jimmie D Weaver; Antonio Recio; Alexander J Grenning; Jon A Tunge
Journal:  Chem Rev       Date:  2011-01-14       Impact factor: 60.622

3.  Enantioselective, Catalytic Fluorolactonization Reactions with a Nucleophilic Fluoride Source.

Authors:  Eric M Woerly; Steven M Banik; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2016-10-13       Impact factor: 15.419

4.  Catalytic Addition of Simple Alkenes to Carbonyl Compounds Using Group 10 Metals.

Authors:  Chun-Yu Ho; Kristin D Schleicher; Timothy F Jamison
Journal:  Synlett       Date:  2009-10-01       Impact factor: 2.454

5.  Catalytic Diastereo- and Enantioselective Fluoroamination of Alkenes.

Authors:  Katrina M Mennie; Steven M Banik; Elaine C Reichert; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2018-03-29       Impact factor: 15.419

Review 6.  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 7.  Asymmetric ion-pairing catalysis.

Authors:  Katrien Brak; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-28       Impact factor: 15.336

8.  Recyclable fluorous cinchona alkaloid ester as a chiral promoter for asymmetric fluorination of β-ketoesters.

Authors:  Wen-Bin Yi; Xin Huang; Zijuan Zhang; Dian-Rong Zhu; Chun Cai; Wei Zhang
Journal:  Beilstein J Org Chem       Date:  2012-08-03       Impact factor: 2.883

9.  Development of the titanium-TADDOLate-catalyzed asymmetric fluorination of β-ketoesters.

Authors:  Lukas Hintermann; Mauro Perseghini; Antonio Togni
Journal:  Beilstein J Org Chem       Date:  2011-10-17       Impact factor: 2.883

10.  Stereoselective alpha-fluoroamide and alpha-fluoro-gamma-lactone synthesis by an asymmetric zwitterionic aza-Claisen rearrangement.

Authors:  Kenny Tenza; Julian S Northen; David O'Hagan; Alexandra M Z Slawin
Journal:  Beilstein J Org Chem       Date:  2005-10-17       Impact factor: 2.883
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