Literature DB >> 22588851

Ruthenium-catalyzed redox isomerization of trifluoromethylated allylic alcohols: mechanistic evidence for an enantiospecific pathway.

Vincent Bizet1, Xavier Pannecoucke, Jean-Luc Renaud, Dominique Cahard.   

Abstract

Transfer news: A synthetic approach to chiral β-CF(3)-substituted saturated carbonyl compounds has been developed in which ruthenium complexes efficiently catalyze the redox isomerization of CF(3)-bearing allylic alcohols by an intramolecular suprafacial enantiospecific 1,3-hydrogen transfer (see scheme). This method was used for the enantioselective synthesis of (S)-CF(3)-citronellol.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Year:  2012        PMID: 22588851     DOI: 10.1002/anie.201200827

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


  7 in total

1.  Stereoretentive Deuteration of α-Chiral Amines with D2O.

Authors:  Lillian V A Hale; Nathaniel K Szymczak
Journal:  J Am Chem Soc       Date:  2016-10-06       Impact factor: 15.419

2.  Base-promoted isomerization of CF3-containing allylic alcohols to the corresponding saturated ketones under metal-free conditions.

Authors:  Yoko Hamada; Tomoko Kawasaki-Takasuka; Takashi Yamazaki
Journal:  Beilstein J Org Chem       Date:  2017-08-01       Impact factor: 2.883

3.  Synthesis of α,γ-Chiral Trifluoromethylated Amines through the Stereospecific Isomerization of α-Chiral Allylic Amines.

Authors:  Víctor García-Vázquez; Pablo Martínez-Pardo; Alexandru Postole; A Ken Inge; Belén Martín-Matute
Journal:  Org Lett       Date:  2022-05-19       Impact factor: 6.072

4.  Asymmetric allylic substitution-isomerization to axially chiral enamides via hydrogen-bonding assisted central-to-axial chirality transfer.

Authors:  Chao Sun; Xiaotian Qi; Xiao-Long Min; Xue-Dan Bai; Peng Liu; Ying He
Journal:  Chem Sci       Date:  2020-09-07       Impact factor: 9.825

5.  Iridium-catalyzed 1,3-hydrogen shift/chlorination of allylic alcohols.

Authors:  Nanna Ahlsten; Antonio Bermejo Gómez; Belén Martín-Matute
Journal:  Angew Chem Int Ed Engl       Date:  2013-04-24       Impact factor: 15.336

6.  Oxidative 3,3,3-trifluoropropylation of arylaldehydes.

Authors:  Akari Ikeda; Masaaki Omote; Shiho Nomura; Miyuu Tanaka; Atsushi Tarui; Kazuyuki Sato; Akira Ando
Journal:  Beilstein J Org Chem       Date:  2013-11-11       Impact factor: 2.883

7.  Highly Efficient Kinetic Resolution of Aryl-Alkenyl Alcohols by Ru-Catalyzed Hydrogen Transfer.

Authors:  Yipeng You; Ming Yu Jin; Guanyu Tao; Xiangyou Xing
Journal:  Molecules       Date:  2021-12-10       Impact factor: 4.411

  7 in total

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