Literature DB >> 27934501

Orthogonally Protected 1,2-Diols from Electron-Rich Alkenes Using Metal-Free Olefin syn-Dihydroxylation.

Ignacio Colomer1, Rosimeire Coura Barcelos1, Kirsten E Christensen1, Timothy J Donohoe1.   

Abstract

A new method for the stereoselective metal-free syn-dihydroxylation of electron-rich olefins is reported, involving reaction with TEMPO/IBX in trifluoroethanol (TFE) or hexafluoroisopropanol (HFIP) and the addition of a suitable nucleophile. Orthogonally protected syn 1,2-diols were obtained with high levels of diastereocontrol, and these products were selectively deprotected and selectively functionalized into synthetically useful compounds.

Entities:  

Year:  2016        PMID: 27934501     DOI: 10.1021/acs.orglett.6b02959

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


  1 in total

1.  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

  1 in total

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