Literature DB >> 11554838

A very mild and chemoselective oxidation of alcohols to carbonyl compounds.

L De Luca1, G Giacomelli, A Porcheddu.   

Abstract

Efficient oxidation of primary alcohols and beta-amino alcohols to the corresponding aldehydes and alpha-amino aldehydes can be carried out at room temperature and in methylene chloride, using trichloroisocyanuric acid in the presence of catalytic TEMPO: aliphatic, benzylic, and allylic alcohols, and beta-amino alcohols are rapidly oxidized without no overoxidation to carboxylic acids. Secondary carbinols are slowly oxidized so that the reaction is highly chemoselective. Reaction: see text.

Entities:  

Year:  2001        PMID： 11554838     DOI： 10.1021/ol016501m

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  10 in total

1.  Synthesis and Evaluation of Fluoroalkyl Phosphonyl Analogues of 2- C-Methylerythritol Phosphate as Substrates and Inhibitors of IspD from Human Pathogens.

Authors:  David Bartee; Michael J Wheadon; Caren L Freel Meyers
Journal:  J Org Chem       Date:  2018-06-11       Impact factor: 4.354

2.  Diastereoselective nitrenium ion-mediated cyclofunctionalization: total synthesis of (+)-castanospermine.

Authors:  Edward G Bowen; Duncan J Wardrop
Journal:  Org Lett       Date:  2010-10-21       Impact factor: 6.005

Review 3.  Chemoselective hydroxyl group transformation: an elusive target.

Authors:  Darci J Trader; Erin E Carlson
Journal:  Mol Biosyst       Date:  2012-10

4.  Substituted Aryl Benzylamines as Potent and Selective Inhibitors of 17β-Hydroxysteroid Dehydrogenase Type 3.

Authors:  Nigel Vicker; Helen V Bailey; Joanna M Day; Mary F Mahon; Andrew Smith; Helena J Tutill; Atul Purohit; Barry V L Potter
Journal:  Molecules       Date:  2021-11-26       Impact factor: 4.411

5.  Synthesis and initial evaluation of quinoline-based inhibitors of the SH2-containing inositol 5'-phosphatase (SHIP).

Authors:  Christopher M Russo; Arijit A Adhikari; Daniel R Wallach; Sandra Fernandes; Amanda N Balch; William G Kerr; John D Chisholm
Journal:  Bioorg Med Chem Lett       Date:  2015-09-15       Impact factor: 2.823

6.  Aromatase and dual aromatase-steroid sulfatase inhibitors from the letrozole and vorozole templates.

Authors:  Paul M Wood; L W Lawrence Woo; Mark P Thomas; Mary F Mahon; Atul Purohit; Barry V L Potter
Journal:  ChemMedChem       Date:  2011-05-23       Impact factor: 3.466

7.  Metal-free mechanochemical oxidations in Ertalyte® jars.

Authors:  Andrea Porcheddu; Francesco Delogu; Lidia De Luca; Claudia Fattuoni; Evelina Colacino
Journal:  Beilstein J Org Chem       Date:  2019-07-25       Impact factor: 2.883

8.  Mechanically induced oxidation of alcohols to aldehydes and ketones in ambient air: Revisiting TEMPO-assisted oxidations.

Authors:  Andrea Porcheddu; Evelina Colacino; Giancarlo Cravotto; Francesco Delogu; Lidia De Luca
Journal:  Beilstein J Org Chem       Date:  2017-10-02       Impact factor: 2.883

9.  The preparation of new phosphorus-centered functional groups for modified oligonucleotides and other natural phosphates.

Authors:  Arnaud Gautier; Chrystel Lopin; Goulnara Garipova; Olivier Dubert; Irina Kalinina; Carmen Salcedo; Sébastien Balieu; Stéphane Glatigny; Jean-Yves Valnot; Géraldine Gouhier; Serge R Piettre
Journal:  Molecules       Date:  2005-09-30       Impact factor: 4.411

10.  4-Methyltetrahydropyran (4-MeTHP): Application as an Organic Reaction Solvent.

Authors:  Shoji Kobayashi; Tomoki Tamura; Saki Yoshimoto; Takashi Kawakami; Araki Masuyama
Journal:  Chem Asian J       Date:  2019-10-16
  10 in total

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