Literature DB >> 27023314

Access to Diverse Oxygen Heterocycles via Oxidative Rearrangement of Benzylic Tertiary Alcohols.

Brandon T Kelley1, Jennifer C Walters1, Sarah E Wengryniuk1.   

Abstract

A facile method for the synthesis of challenging medium-sized cyclic ethers has been developed via a novel oxidative rearrangement of benzylic tertiary alcohols. The reaction provides access to cyclic acetals with diverse substitution at both C2 and the aromatic ring. The unique reactivity is enabled by poly(cationic) hypervalent iodine reagents and represents the first synthetic application of this underexplored class of compounds.

Entities:  

Year:  2016        PMID： 27023314     DOI： 10.1021/acs.orglett.6b00672

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


  14 in total

1.  Enantio- and Diastereoselective, Lewis Base Catalyzed, Cascade Sulfenoacetalization of Alkenyl Aldehydes.

Authors:  Anastassia Matviitsuk; Scott E Denmark
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-01       Impact factor: 15.336

2.  Hexafluoroisopropanol mediated benign synthesis of 2H-pyrido[1,2-a]pyrimidin-2-ones by using a domino protocol.

Authors:  Zakeyah Alsharif; Mohamad Akbar Ali; Hessa Alkhattabi; Derika Jones; Evan Delancey; P C Ravikumar; Mohammad A Alam
Journal:  New J Chem       Date:  2017-10-20       Impact factor: 3.591

3.  Direct C-H α-Arylation of Enones with ArI(O2CR)2 Reagents.

Authors:  Felipe Cesar Sousa E Silva; Nguyen T Van; Sarah E Wengryniuk
Journal:  J Am Chem Soc       Date:  2019-12-27       Impact factor: 15.419

4.  Chemoselective Oxidation of Equatorial Alcohols with N-Ligated λ3-Iodanes.

Authors:  Myriam Mikhael; Sophia A Adler; Sarah E Wengryniuk
Journal:  Org Lett       Date:  2019-07-16       Impact factor: 6.005

5.  Dearomatization of Electron-Deficient Phenols to ortho-Quinones: Bidentate Nitrogen-Ligated Iodine(V) Reagents.

Authors:  Xiao Xiao; Nathaniel S Greenwood; Sarah E Wengryniuk
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-20       Impact factor: 15.336

6.  Synthesis of Enantioenriched 3,4-Disubstituted Chromans through Lewis Base Catalyzed Carbosulfenylation.

Authors:  Travis Menard; Aragorn Laverny; Scott E Denmark
Journal:  J Org Chem       Date:  2021-10-21       Impact factor: 4.354

7.  Preparation of (Bis)Cationic Nitrogen-Ligated I(III) Reagents: Synthesis of [(pyridine)2IPh](OTf)2 and [(4-CF3-pyridine)2IPh](OTf)2.

Authors:  Bilal Hoblos; Sarah E Wengryniuk
Journal:  Organic Synth       Date:  2021-10-20

8.  (Poly)cationic λ3-Iodane Mediated Oxidative Ring Expansion of Secondary Alcohols.

Authors:  Jennifer C Walters; Anthony F Tierno; Aimee H Dubin; Sarah E Wengryniuk
Journal:  European J Org Chem       Date:  2018-01-31

9.  Use of hydroxylamines, hydroxamic acids, oximes and amines as nucleophiles in the Zbiral oxidative deamination of N-acetyl neuraminic acid. Isolation and characterization of novel mono- and disubstitution products.

Authors:  Mohammed Hawsawi; Michael G Pirrone; Anura Wickramasinghe; David Crich
Journal:  Carbohydr Res       Date:  2020-01-25       Impact factor: 2.104

10.  Recent Advances in the Selective Oxidative Dearomatization of Phenols to o-Quinones and o-Quinols with Hypervalent Iodine Reagents.

Authors:  Xiao Xiao; Sarah E Wengryniuk
Journal:  Synlett       Date:  2021-01-14       Impact factor: 2.454
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