Literature DB >> 24214871

Kinetic resolution of allyl fluorides by enantioselective allylic trifluoromethylation based on silicon-assisted C-F bond cleavage.

Takayuki Nishimine1, Kazunobu Fukushi, Naoyuki Shibata, Hiromi Taira, Etsuko Tokunaga, Akihito Yamano, Motoo Shiro, Norio Shibata.   

Abstract

Two birds, one stone! The first kinetic resolution of allyl fluorides was achieved by the development of an organocatalyzed enantioselective allylic trifluoromethylation. Two kinds of chiral fluorinated compounds, which incorporate C*F and C*CF3 units, respectively, can thus be accessed by a single transformation.
Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  allyl fluorides; fluorine; kinetic resolution; organocatalysis; trifluoromethylation

Mesh：

Substances：

Year:  2013        PMID： 24214871     DOI： 10.1002/anie.201308071

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


  7 in total

1.  Stereoconvergent Negishi Arylations of Racemic Secondary Alkyl Electrophiles: Differentiating between a CF3 and an Alkyl Group.

Authors:  Yufan Liang; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2015-07-23       Impact factor: 15.419

2.  Palladium and Nickel Catalyzed Suzuki Cross-Coupling with Alkyl Fluorides.

Authors:  Kaluvu Balaraman; Christian Wolf
Journal:  Org Lett       Date:  2021-11-01       Impact factor: 6.005

3.  Chemodivergent Csp3─F bond functionalization and cross-electrophile alkyl-alkyl coupling with alkyl fluorides.

Authors:  Kaluvu Balaraman; Christian Wolf
Journal:  Sci Adv       Date:  2022-05-27       Impact factor: 14.957

4.  Asymmetric Traceless Petasis Borono-Mannich Reactions of Enals: Reductive Transposition of Allylic Diazenes.

Authors:  Yao Jiang; Regan J Thomson; Scott E Schaus
Journal:  Angew Chem Int Ed Engl       Date:  2017-12-04       Impact factor: 15.336

Review 5.  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

6.  Sterically Demanding Unsymmetrical Diaryl-λ(3)-iodanes for Electrophilic Pentafluorophenylation and an Approach to α-Pentafluorophenyl Carbonyl Compounds with an All-Carbon Stereocenter.

Authors:  Kohei Matsuzaki; Kenta Okuyama; Etsuko Tokunaga; Motoo Shiro; Norio Shibata
Journal:  ChemistryOpen       Date:  2014-09-17       Impact factor: 2.911

7.  Catalytic enantioselective synthesis of fluoromethylated stereocenters by asymmetric hydrogenation.

Authors:  Jianping Yang; Sudipta Ponra; Xingzhen Li; Bram B C Peters; Luca Massaro; Taigang Zhou; Pher G Andersson
Journal:  Chem Sci       Date:  2022-06-29       Impact factor: 9.969
  7 in total

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