Literature DB >> 16729117

Catalytic asymmetric fluorinations.

Carla Bobbio1, Véronique Gouverneur.   

Abstract

The appearance of structurally diverse fluorinating reagents displaying a large spectrum of reactivity has been critical to the development of the catalytic asymmetric fluorination processes known to date. In this article, we discuss how this area of research emerged and which strategies have allowed for the successful development of both nucleophilic and electrophilic catalytic enantioselective fluorinations. We also present the fundamental understanding of catalytic activity and enantioselectivity for the most efficient processes and highlight the first synthetic application with the preparation of a complex fluorinated target.

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Year:  2006        PMID: 16729117     DOI: 10.1039/b603163c

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  16 in total

1.  Stereoselective synthesis of alpha,alpha-chlorofluoro carbonyl compounds leading to the construction of fluorinated chiral quaternary carbon centers.

Authors:  Kazutaka Shibatomi; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

2.  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

3.  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

4.  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

5.  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

6.  Enantioselective Formation of CF3-Bearing All-Carbon Quaternary Stereocenters via C-H Functionalization of Methanol: Iridium Catalyzed Allene Hydrohydroxymethylation.

Authors:  Michael Holmes; Khoa D Nguyen; Leyah A Schwartz; Tom Luong; Michael J Krische
Journal:  J Am Chem Soc       Date:  2017-06-12       Impact factor: 15.419

7.  Iridium-catalyzed anti-diastereo- and enantioselective carbonyl (α-trifluoromethyl)allylation from the alcohol or aldehyde oxidation level.

Authors:  Xin Gao; Yong Jian Zhang; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-06       Impact factor: 15.336

8.  Chemo-enzymatic fluorination of unactivated organic compounds.

Authors:  Andrea Rentmeister; Frances H Arnold; Rudi Fasan
Journal:  Nat Chem Biol       Date:  2008-11-16       Impact factor: 15.040

9.  Palladium-Catalyzed Enantioselective Csp3-Csp3 Cross-Coupling for the Synthesis of (Poly)fluorinated Chiral Building Blocks.

Authors:  Yanhui Lu; Elizabeth L Goldstein; Brian M Stoltz
Journal:  Org Lett       Date:  2018-09-05       Impact factor: 6.005

10.  Single and double stereoselective fluorination of (E)-allylsilanes.

Authors:  Marcin Sawicki; Angela Kwok; Matthew Tredwell; Véronique Gouverneur
Journal:  Beilstein J Org Chem       Date:  2007-10-25       Impact factor: 2.883

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