Literature DB >> 20111780

Fluorine & chirality: how to create a nonracemic stereogenic carbon-fluorine centre?

Dominique Cahard1, Xiuhua Xu, Samuel Couve-Bonnaire, Xavier Pannecoucke.   

Abstract

Enantiopure organofluorine compounds are at the forefront of innovation in the field of fluorine chemistry. The significant progress in modern fluoroorganic chemistry parallels the tremendous achievements in organocatalysis and organometallic catalysis that have permitted the asymmetric synthesis of chiral chemicals featuring a fluorinated stereogenic carbon centre. This tutorial review provides an overview of the current state of the art in asymmetric construction of stereogenic carbon-fluorine centres, not only by direct fluorination, but also by asymmetric reaction of fluorinated substrates.

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Year:  2009        PMID: 20111780     DOI: 10.1039/b909566g

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  28 in total

1.  From bifunctional to trifunctional (tricomponent nucleophile-transition metal-lewis acid) catalysis: the catalytic, enantioselective α-fluorination of acid chlorides.

Authors:  Jeremy Erb; Daniel H Paull; Travis Dudding; Lee Belding; Thomas Lectka
Journal:  J Am Chem Soc       Date:  2011-04-22       Impact factor: 15.419

2.  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

3.  Consecutive iridium catalyzed C-C and C-H bond forming hydrogenations for the diastereo- and enantioselective synthesis of syn-3-fluoro-1-alcohols: C-H (2-fluoro)allylation of primary alcohols.

Authors:  Abbas Hassan; T Patrick Montgomery; Michael J Krische
Journal:  Chem Commun (Camb)       Date:  2012-04-04       Impact factor: 6.222

4.  Ruthenium-catalyzed C-C coupling of fluorinated alcohols with allenes: dehydrogenation at the energetic limit of β-hydride elimination.

Authors:  Brannon Sam; Tom Luong; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2015-03-10       Impact factor: 15.336

5.  Selection between Diastereomeric Kinetic vs Thermodynamic Carbonyl Binding Modes Enables Enantioselective Iridium-Catalyzed anti-(α-Aryl)allylation of Aqueous Fluoral Hydrate and Difluoroacetaldehyde Ethyl Hemiacetal.

Authors:  James M Cabrera; Johannes Tauber; Wandi Zhang; Ming Xiang; Michael J Krische
Journal:  J Am Chem Soc       Date:  2018-07-18       Impact factor: 15.419

6.  Enantiodivergent Fluorination of Allylic Alcohols: Data Set Design Reveals Structural Interplay between Achiral Directing Group and Chiral Anion.

Authors:  Andrew J Neel; Anat Milo; Matthew S Sigman; F Dean Toste
Journal:  J Am Chem Soc       Date:  2016-03-11       Impact factor: 15.419

7.  Catalytic Enantioselective Synthesis of Allylic Boronates Bearing a Trisubstituted Alkenyl Fluoride and Related Derivatives.

Authors:  Sota Akiyama; Koji Kubota; Malte S Mikus; Paulo H S Paioti; Filippo Romiti; Qinghe Liu; Yuebiao Zhou; Amir H Hoveyda; Hajime Ito
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-16       Impact factor: 15.336

8.  Asymmetric catalytic Mannich-type reaction of hydrazones with difluoroenoxysilanes using imidazoline-anchored phosphine ligand-zinc(II) complexes.

Authors:  Zhiliang Yuan; Liangyong Mei; Yin Wei; Min Shi; Padmanabha V Kattamuri; Patrick McDowell; Guigen Li
Journal:  Org Biomol Chem       Date:  2012-02-15       Impact factor: 3.876

9.  Catalytic enantioselective cyclization and C3-fluorination of polyenes.

Authors:  Nikki A Cochrane; Ha Nguyen; Michel R Gagne
Journal:  J Am Chem Soc       Date:  2013-01-08       Impact factor: 15.419

10.  Cyclometalated Iridium-PhanePhos Complexes Are Active Catalysts in Enantioselective Allene-Fluoral Reductive Coupling and Related Alcohol-Mediated Carbonyl Additions That Form Acyclic Quaternary Carbon Stereocenters.

Authors:  Leyah A Schwartz; Michael Holmes; Gilmar A Brito; Théo P Gonçalves; Jeffery Richardson; J Craig Ruble; Kuo-Wei Huang; Michael J Krische
Journal:  J Am Chem Soc       Date:  2019-01-25       Impact factor: 15.419

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