Literature DB >> 26284459

Williamson Ether Synthesis with Phenols at a Tertiary Stereogenic Carbon: Formal Enantioselective Phenoxylation of β-Keto Esters.

Kazutaka Shibatomi1, Manato Kotozaki2, Nozomi Sasaki2, Ikuhide Fujisawa2, Seiji Iwasa2.   

Abstract

The enantioselective formation of α-aryloxy-β-keto esters is described for the first time. Lewis acid catalyzed enantioselective chlorination of β-keto esters and subsequent SN 2 reactions with phenols yielded α-aryloxy-β-keto esters with up to 96% ee. Favorskii rearrangement of α-chloro-β-keto esters was also found to give 1,2-diesters with slightly reduced enantiopurity.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric synthesis; enantioselectivity; nucleophilic substitution; phenoxylation; synthesis design

Year:  2015        PMID： 26284459     DOI： 10.1002/chem.201502042

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


  10 in total

1.  Application of 2,4-bis(halomethyl)quinoline: synthesis and biological activities of 2,4-bis(benzofuran-2-yl)- and 2,4-bis(aroxymethyl)quinolines.

Authors:  Yang Li; Qiqi Xu; Zhiyuan Li; Wentao Gao; Yu Chen
Journal:  Mol Divers       Date:  2019-03-20       Impact factor: 2.943

2.  Copper-Catalyzed Synthesis of Hindered Ethers from α-Bromo Carbonyl Compounds.

Authors:  Zhe Zhou; Nicole Erin Behnke; László Kürti
Journal:  Org Lett       Date:  2018-08-16       Impact factor: 6.005

3.  A Diazo-Hooker Reaction, Inspired by the Biosynthesis of Azamerone.

Authors:  Oussama Yahiaoui; Lauren A M Murray; Fengyue Zhao; Bradley S Moore; Kendall N Houk; Fang Liu; Jonathan H George
Journal:  Org Lett       Date:  2022-01-07       Impact factor: 6.005

4.  Synergistic Peptide and Gold Catalysis: Enantioselective Addition of Branched Aldehydes to Allenamides.

Authors:  Leo D M Nicholls; Helma Wennemers
Journal:  Chemistry       Date:  2021-10-13       Impact factor: 5.020

5.  Enantioselective decarboxylative chlorination of β-ketocarboxylic acids.

Authors:  Kazutaka Shibatomi; Kazumasa Kitahara; Nozomi Sasaki; Yohei Kawasaki; Ikuhide Fujisawa; Seiji Iwasa
Journal:  Nat Commun       Date:  2017-06-05       Impact factor: 14.919

6.  Enantioselective fluorination of α-branched aldehydes and subsequent conversion to α-hydroxyacetals via stereospecific C-F bond cleavage.

Authors:  Kazutaka Shibatomi; Kazumasa Kitahara; Takuya Okimi; Yoshiyuki Abe; Seiji Iwasa
Journal:  Chem Sci       Date:  2015-11-16       Impact factor: 9.825

7.  Stereoselective α-Chlorination of β-Keto Esters in the Presence of Hybrid Amide-Based Cinchona Alkaloids as Catalysts.

Authors:  Maciej Majdecki; Piotr Grodek; Janusz Jurczak
Journal:  J Org Chem       Date:  2020-12-15       Impact factor: 4.354

8.  Enantioselective Catalytic Synthesis of α-Halogenated α-Aryl-β2,2-amino Acid Derivatives.

Authors:  Paul Zebrowski; Isabella Eder; Andreas Eitzinger; Sharath Chandra Mallojjala; Mario Waser
Journal:  ACS Org Inorg Au       Date:  2021-09-24

Review 9.  Chiral phase-transfer catalysis in the asymmetric α-heterofunctionalization of prochiral nucleophiles.

Authors:  Johannes Schörgenhumer; Maximilian Tiffner; Mario Waser
Journal:  Beilstein J Org Chem       Date:  2017-08-22       Impact factor: 2.883

10.  Asymmetric Synthesis of Tertiary α -Hydroxyketones by Enantioselective Decarboxylative Chlorination and Subsequent Nucleophilic Substitution.

Authors:  Mei Kee Kam; Akira Sugiyama; Ryouta Kawanishi; Kazutaka Shibatomi
Journal:  Molecules       Date:  2020-08-27       Impact factor: 4.411
  10 in total

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