Literature DB >> 21294172

Enantioselective organocatalytic synthesis of fluorinated molecules.

Guillem Valero1, Xavier Companyó, Ramon Rios.   

Abstract

The enantioselective synthesis of fluorinated molecules has drawn much attention within the chemical community due to its unique stereoelectronic properties. The main aim of this review is to cover the most important organocatalytic enantioselective methodologies to obtain them. The review is divided into three parts: first, the direct introduction of a fluorine atom studied in the early 2000s. Second, the later use of Michael reactions to introduce fluorine-containing synthons. Finally, the simultaneously-developed trifluoromethylation reactions, giving the catalysts, mechanisms and reagents that have been used.
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Year:  2011        PMID: 21294172     DOI: 10.1002/chem.201001546

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  13 in total

1.  An organocatalytic strategy for the stereoselective synthesis of C-galactosides with fluorine at the pseudoanomeric carbon.

Authors:  Ahmad S Altiti; S Bachan; W Alrowhani; D R Mootoo
Journal:  Org Biomol Chem       Date:  2015-11-07       Impact factor: 3.876

Review 2.  The ever-expanding role of asymmetric covalent organocatalysis in scalable, natural product synthesis.

Authors:  Mikail E Abbasov; Daniel Romo
Journal:  Nat Prod Rep       Date:  2014-10       Impact factor: 13.423

3.  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

4.  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

5.  Enantioselective nucleophile-catalyzed synthesis of tertiary alkyl fluorides via the α-fluorination of ketenes: synthetic and mechanistic studies.

Authors:  Sarah Yunmi Lee; Stefan Neufeind; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2014-06-12       Impact factor: 15.419

6.  Catalytic asymmetric synthesis of tertiary alkyl fluorides: Negishi cross-couplings of racemic α,α-dihaloketones.

Authors:  Yufan Liang; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2014-03-31       Impact factor: 15.419

Review 7.  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

8.  Syntheses and Applications of (Thio)Urea-Containing Chiral Quaternary Ammonium Salt Catalysts.

Authors:  Johanna Novacek; Mario Waser
Journal:  European J Org Chem       Date:  2014-02

9.  An in situ directing group strategy for chiral anion phase-transfer fluorination of allylic alcohols.

Authors:  Weiwei Zi; Yi-Ming Wang; F Dean Toste
Journal:  J Am Chem Soc       Date:  2014-09-09       Impact factor: 15.419

10.  How cinchona alkaloid-derived primary amines control asymmetric electrophilic fluorination of cyclic ketones.

Authors:  Yu-hong Lam; K N Houk
Journal:  J Am Chem Soc       Date:  2014-06-26       Impact factor: 15.419

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